


Purgatory

by songofhell



Series: Just Business [1]
Category: Supernatural
Genre: Canon-Typical Violence, M/M, Prison AU, denny is more friends with benefits, drowley is the main ship
Language: English
Status: Completed
Published: 2017-06-19
Updated: 2017-10-26
Packaged: 2018-11-16 03:34:50
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 16
Words: 35,255
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11245479
Author URL: https://archiveofourown.org/users/songofhell/pseuds/songofhell
Summary: Dean had heard stories about the prison he would be doing his time in, and none of them were good. Sure, the prisoners were bad, but from what he’d heard, some of the guards were even worse.When Dean was put in a prison so bad that the inmates had nicknamed it 'Purgatory,' he knew that things would not be good for him. What he hadn't excepted was the special interest that all of the guards seemed to be taking in him - Alastair and Crowley, in particular. And while Crowley's attention is certainly better than Alastair's, Dean's still not about to give in to him - at least, that's what he keeps telling himself. But hey, at least his cellmate is alright.





	1. Welcome to Purgatory

**Author's Note:**

> So, AUs aren't generally my thing, but I decided to give it a go. I don't watch a lot of prison shows or anything like that, so sorry if the prison life is terribly inaccurate.

Dean knew that he was in trouble. Deep trouble. And maybe he should feel guilty, maybe it should be weighing on him that he had killed a guy, but the way he saw it, he had done what he had to do. Everyone knew who Dick Roman was these days – or rather, who he had been – a wealthy businessman on the rise who could do no harm, as far as society was concerned. Except Dean’s little brother, Sam, had been doing a school project on Dick’s company, and he saw something he shouldn’t have. Dick had been about to dispose of him quietly and make it look like an accident, when Dean showed up and killed him first. So, now he was sitting in the courtroom, awaiting the jury’s verdict; though, he already knew what it would be.

Of course, he tried to pass it off as self-defense, but the fact was, he had a record. His mom had died when he was young, and it had taken a toll on his dad. He knew his dad tried, he really did, but they still barely had enough to get by. He just wanted his little brother to have a good life; so, he had gotten into the habit of stealing so that Sam could have at least _something_ nice. He had gotten caught a couple of times when he was younger, and while the consequences hadn’t been too bad, his history as a juvenile delinquent wouldn’t do him any favors today… especially considering the guy he had killed was one of the most respectable men in America. Even without his record, there was no way he’d be walking out of this one.

When the verdict was delivered and the judge read him his sentence, he just nodded, the only thought going through his mind that he would no longer be around to protect Sammy.

“Dean,” Sam’s voice broke as he walked up to him, alongside their father. “This is all my fault.”

“No,” Dean said firmly. “Sam, you aren’t to blame for this. That man was a monster – he got what he deserved.”

John clapped a hand on Dean’s shoulder. “It should’ve been me, not you, that had to do that.”

He shrugged. “It is what it is. You just take good care of him.” He nodded to his little brother.

“Of course I will,” he said solemnly.

“Dean, come on,” Sam sighed. “I’m nearly an adult, I don’t need to be taken care of – I’m not who you should be worrying about, here.”

Dean rolled his eyes. “You’re seventeen, that’s not an adult.”

“That’s not what you said when you were seventeen.”

“Yeah, and I don’t want you pulling the same shit I did when I was seventeen. You work hard in school, get a scholarship, get into Stanford.”

Sam nodded, trying to manage a small smile. “I’ll do my best.”

“Well, with your best, you’ll be a shoo-in.”

“We’ll come visit you. Right, Dad?” He looked at John with an expression that they all knew meant that he wasn’t really asking permission.

“As often as we will,” John promised.

They all looked over as Sheriff Mills cleared her throat and stepped over to them, her expression sympathetic. “I’m sorry, but it’s time to go.”

Dean swallowed thickly as he looked back at his dad, a desperate look in his eyes. He had been so focused on the trial that he hadn’t allowed himself to think of what would come after. He had never viewed fear as a bad thing – he had always been able to do something with his fear, to make something out of it. Fear could spur you to do things that you never would have thought yourself capable – like killing a man, for instance. But right now, there wasn’t anything he could do with his fear. He couldn’t fight back, he couldn’t avoid it – he was going to prison, going to be separated from his family, and he was terrified.

“Keep your head down, son,” John advised softly. “Don’t draw attention to yourself. Try to behave and not to mouth off so much, and you could get an early release.”

Dean opened his mouth to speak, but the words wouldn’t come, so he just nodded. His dad reached out and pulled him into a hug.

“Take care of yourself,” John muttered.

As soon as he released him, Sam threw his arms around his older brother, holding onto him tightly. Dean found that he had to take a deep breath to stop himself from crying. “You be good, Sammy,” he muttered, patting him on the back before pulling away. “I’ll be fine,” he assured him as he turned to go with the sheriff, hating to think that the next time he’d be seeing his brother, there’d be a pane of glass between them.

Dean had heard stories about the prison he would be doing his time in, and none of them were good. Sure, the prisoners were bad, but from what he’d heard, some of the guards were even worse. When his dad had heard the confirmation of where Dean would be going if he was convicted, he threw a fit – said that he wanted to keep Dean out of there at all costs. Even Dean thought that was a little extreme, but his dad just said that he had his reasons for not wanting him there. Clearly, he hadn’t gotten his way.

When Dean arrived at the prison, he got changed into his jumpsuit and then was led to a guard who didn’t look like he could be much older than him. While his expression was serious, his face seemed kind, but Dean knew better than to trust that here. “Dean Winchester?” the guard greeted him. “I’m Castiel.”

“Wish I could say it’s good to meet you, but frankly, it isn’t. Sorry,” Dean said with a shrug. Hey, points for honesty, right?

Castiel smiled slightly. “Well, at least you’re more polite than most people I greet.”

He quirked a half-smile. “What can I say? I want to get out of here as soon as possible.”

He nodded understandingly. “Someone you’re wanting to get back to?”

Dean hesitated, not too fond of the idea of opening up to a prison guard, even if just a little bit. But he had been taking the honest route so far, and maybe it could gain him some sympathy – assuming this guy was actually capable of such a thing, but so far, he didn’t seem so bad. “My little brother. Our dad’s still around, but I was always the one to look out for him. I don’t like the thought of not being there for him.”

“I’m sorry to hear that.” His voice sounded sincere, at least. He tilted his head to the side curiously. “You don’t come across as a killer, Dean.”

He chuckled. “Wish you had been in the jury.”

“Do you mind if I ask what happened?”

“He was going to kill my brother. I didn’t have a choice.”

Castiel nodded. “Well, I wish it were him that I was showing to a cell, instead of you. If you’ll follow me.”

Dean fell into step beside Castiel as he was led through the prison. “So, how long you been working here?” he asked conversationally.

“About a year.”

“You like it?”

Castiel smiled wryly. “No.”

“So, why do it?”

He looked at him thoughtfully. “Because I want to make a difference.”

“There are much nicer ways to make a difference,” Dean pointed out.

“There are,” he conceded with a nod. “But if everyone has that mindset, then no one will ever seek to make a difference in the places that aren’t so nice.”

“Guess that’s true. So, have you made much of a difference here?”

“I would like to think so. But only a small one – this is not a place where making a difference is easy.”

“Yeah, I kinda figured.” Maybe Castiel wasn’t so bad – that was, if he was referring to making a difference in the corrupt way things were run here, and not in beating even more prisoners to death. But somehow, Dean couldn’t see him doing the latter. And he was actually treating him like a human being, so that said something.

 “What is your brother’s name?” Castiel asked after a few seconds of silence.

“Sam,” Dean said, sadness subduing his voice slightly. Sam was a smart kid, and odds were he would be just fine, but that didn’t change that being separated from his little brother just felt _wrong._ He should be there for him – be looking out for him, just like he always had.

Castiel gave him a small, sad smile. “He’s in school?”

“Yeah – about to start his senior year.”

“Is he planning on going to college?” he asked conversationally.

“Yeah, Stanford, if he can get in. Which, with his brains, I know he can – it’ll just be a matter of him getting enough scholarships to afford it,” he sighed. More than anything, he just wanted Sam to have a good life – he’d gladly spend the rest of his life in this place, if it meant that.

“I-”

“Cassie!” A voice interrupted, and Dean looked over to see a shorter guard approaching them. “Making friendly with the prisoners, again?”

Castiel smiled slightly as he turned to the other guard. “Hello, Gabriel. Dean, this is my older brother, Gabriel.”

“Hi,” Dean greeted him.

Gabriel glanced at Dean with a roll of his eyes before he returned his attention to his brother. “You’re wanted in for review – again.”

Castiel sighed. “What is it this time?”

“Alastair. You have got to start watching your step, Cassie.”

His eyes narrowed. “I have not done anything wrong. Alastair, on the other hand-”

“I know!” Gabriel held up his hands in a pacifying gesture. “I can’t stand the guy, either, but I’m not about to get in his way. He’s been here longer than anyone – you can’t beat him.”

“I can’t stand by and watch, either,” Castiel said coolly.

“Then you’ll lose your job. I’m trying to stick up for you, but I only have so much sway here.”

“I know,” he sighed. “I’ll try to be more careful.”

“Thank you.”

“Who’s Alastair?” Dean piped up curiously.

Gabriel turned to him with a slight grimace. “Keep your head down, and hopefully you won’t find out.”

“Well, that’s not ominous at all.”

He grinned as he turned back to Castiel. “You should probably head to the office after you take him to his cell.”

Castiel nodded. “I will. Come on, Dean.” He continued down the hall, with Dean following behind him.

“So, you work with your brother?” Dean asked once they were out of earshot of Gabriel. “That could get irritating.”

“It does,” he admitted. “But it has its good days, too. Here is your cell.” They came to a stop in front of the last cell on the block. There was a man lounging on the top bunk, but he rolled out of bed when he heard Castiel speak.

“Castiel,” he greeted in a southern drawl that Dean, who had always had a thing for accents, had to admit was pretty damn sexy – matching right up with the man behind the voice.

“Benny,” Castiel nodded to him as he unlocked the cell. “This is Dean.”

Benny looked over at Dean, sizing him up as he entered the cell. “Hello, Dean.”

“Hey,” Dean said, feeling slightly uneasy as he heard the cell being closed behind him, but he didn’t let it show on his face. He just smiled at the man he was now locked in a cell with – a man who looked plenty capable if he were to choose to try to overpower him.

“Have a good night, Dean,” Castiel said as he turned to go.

“Yeah,” he nodded towards him without quite taking his eyes off Benny. “Good luck with your review-thing.”

Benny regarded him with an amused expression as he turned his full attention back to him. “So. Welcome to Purgatory.”

Dean arched an eyebrow at him. “Purgatory? Really?”

He grinned. “Well, we’re not dead, but we’re not truly alive in here, either, are we?”

He chuckled. “Yeah, guess so.” Determined to appear relaxed, he walked over to take a seat on the bottom bunk.

“What’re you in for?”

“I killed Dick Roman.” At least that was guaranteed to make an impression.

Benny whistled. “Not what I was expectin’. What’d he do to you?”

“Nothing. But he was about to kill my brother.”

“So, the hero gets sent to prison. Sounds about right.”

Dean eyed him appraisingly, trying to get a read on him. “What about you?”

“I was stupid. Got involved with the wrong people.”

He frowned curiously. “What kind of people?”

“Pirates,” Benny said with a shrug.

“You’re kidding,” Dean laughed, his lips curling up in a small smile. “You’re an actual pirate?”

“Was,” he corrected. “I was tryin’ to get away from the life when I was arrested.”

“That sucks, man. How long you been in here?”

“A couple years.”

Dean hesitated. He didn’t really want to hear the answer to his next question, but he needed to know. “Is it really as bad as they say?”

Benny’s expression darkened. “Let’s just say, there’s more than one reason it’s nicknamed Purgatory.”


	2. First Impressions

Dean hadn’t been sure what to expect from his cellmate, but he certainly hadn’t figured he’d be lucky enough to get stuck with someone he’d actually get along with. Benny was alright, though – he had a good sense of humor, seemed to be a decent human being, and he was actually making an effort to ensure that Dean survived Purgatory. The next morning at breakfast, he pointed out the prisoners that Dean shouldn’t cross and filled him in on all of the guards.

“Okay, I gotta ask,” Dean started as he finished the last of his food – which wasn’t all that bad, really. “Why do you care that I know all this?”

Benny chuckled. “Because if I’m standing next to you, I don’t want you to piss the wrong guy off and to end up getting caught in the crossfire.”

He laughed. “Okay, fair enough. Carry on,” he added with a wave of his hand.

“Let’s see…” He looked around the cafeteria thoughtfully. “Castiel was who showed you in…”

“Yeah, he seemed nice enough.”

He nodded. “He’s one of the better guards. But if you ask me, he’s not cut out for this place.”

“Yeah, it sounded like he was in trouble yesterday.” At least he was still there, so he clearly hadn’t been fired – Dean would hate to see one of the only decent guards go.

“Doesn’t surprise me. Don’t get me wrong, he’s no softie, but this isn’t a good environment for someone who cares too much.”

Dean nodded understandingly. “What about his brother – Gabriel?”

“He’s alright,” Benny said as his eyes shifted to where Gabriel was talking to a dark-skinned guard. “Cruel sense of humor, though. That’s Uriel he’s talking to, and he’s a real piece of work. One of those high-and-mighty guards who thinks he’s so much better than all of us. If you ask me, this wasn’t what he expected to be doing with his life, and so he takes it out on us.”

“Great,” he sighed.

He turned to him with a bitter grin. “Believe me, it’s nowhere near as bad as the guards who actually _want_ to be here.”

Dean arched an eyebrow. “Like?”

“Don’t let him catch you lookin’, but do you see the guy by the food line?”

He looked over in that direction and nodded as he spotted the guard surveying the inmates with narrowed eyes and a slight grin. “Yeah.”

“Alastair. He’s as bad as anyone in this place, and he’s who runs the show. This is his dream job; been here longer than anyone, and he’s been offered better jobs, but he keeps turnin’ them down. If he weren’t a prison guard, he’d be a serial killer – one of the ones that strings up his victims and tortures them for days.”

So that was who Castiel and Gabriel had been talking about. He certainly didn’t look like someone Dean would want to invite over for dinner. “Stay away from him. Got it. Anyone else I should worry about?”

Benny’s gaze slid to the right and he pointed to someone behind Dean. Turning, Dean saw a slightly older, but still damn attractive guard scanning the tables with a calculating expression. “Crowley,” Benny supplied. “He’s just as bad as Alastair, except a thousand times more subtle. No one really knows what his motivation is. He’ll hurt prisoners if he has to, but… that’s not what he’s about. He’s blackmailed a few, struck deals with others.”

Dean turned back to face him, his expression curious. “What kinds of deals?”

He shrugged. “Dunno. Rumor is he’s runnin’ some sort of crime circle and looking for recruits. Whatever it is, he’s a nasty piece of work.”

He glanced back at him over his shoulder. “Doesn’t seem as bad as Alastair.”

Benny chuckled. “Wait till you see what happens to those who don’t take him up on his deals – not that many are stupid enough to shoot him down. While Alastair is a master at causing physical pain, Crowley looks at the bigger picture. I think he does like beating us, but if he thinks causing misery in some other manner would be more efficient, then that’s what he’ll do. In some ways, he’s even crueler than Alastair.”

Dean quickly turned back to Benny as Crowley began to turn in their direction. “So, what’re the odds that I can slide under their radars?”

“With your pretty face?” he smirked. “Good luck.”

He felt his cheeks heating up slightly at his overtly flirtatious tone. But two could play at that game. “Well, you manage,” he pointed out with a grin.

Benny leaned back in his chair, eyeing him thoughtfully. “You should be careful about who you flirt with here, darlin’.”

“Oh?” He leaned forward to rest his elbows on the table. “And are you one of those people I should be careful around?”

“Depends,” he drawled with a smirk.

“On?”

“If you’re prepared for it to go somewhere.”

Dean felt a shiver run down his spine at the combination of his voice and the intensity of his gaze. Well, this was definitely _not_ something he had anticipated, and frankly, he wasn’t sure how he felt about it. Hooking up with his cellmate? That just sounded like a bad idea. Then again, he was no stranger to bad ideas.

He was saved the trouble of answering, though, as it was time to go to their work assignments.

Benny smiled at him as they got up. “Saved by the bell.”

Dean was assigned to work in the laundry, and all-in-all, it wasn’t so bad. The work wasn’t difficult or tiring, and he got into a routine after a little while. And he didn’t cross paths with either Alastair or Crowley, so he considered it a good day. Or, at least, it was until rec time.

Dean was crossing the yard when a fight broke out – or rather, some asshole started beating up a scrawny guy. A couple hits in, the little guy was unconscious, but the bigger guy kept swinging. Dean hesitated for just a second, before deciding that he didn’t care about the consequences, and he changed direction to sprint over to them.

“Hey!” he shouted. “You wanna take a swing at someone, why don’t you take a swing at me?”

He wasn’t surprised when the guy immediately took him up on his offer – what did catch him off guard was that he was stronger than he looked. Dean managed to get one good swing in, but he was quickly overpowered, and it looked like he was heading in the same direction as the little guy before a guard came over to break them up.

“That’s enough, Connor,” a cool voice said, and Connor responded with a grunt of pain. Dean turned to get a look at his savior and was immediately wishing that he had been knocked out. Alastair’s eyes flickered over him, and even without everything Benny had told him, the look in the guard’s eyes was enough to make Dean’s stomach twist into a knot. “You’re new. What’s your name?”

Dean’s mouth was dry, and he must have hesitated a second too long, because Alastair jabbed Dean in the gut with his baton. “You’ll answer me when I talk to you.”

He coughed, spitting out blood. “Winchester,” he muttered.

Something sparked in Alastair’s eyes and his mouth spread into a twisted smile. “Winchester,” he repeated, savoring the name. “I’d heard you were here – was hoping I’d be making your acquaintance soon.”

Dean looked up in confusion in time for the baton to be brought down across his face. He fell to the ground, seeing stars.

“Leave him be,” Castiel’s voice rang out, drawing closer as he spoke. Dean tried to look up at him, but everything spun around him, so he just squeezed his eyes shut, waiting for his head to stop pounding. “These two men need to be taken to the infirmary.”

“They’re not men. Not in here.” He brought the baton down against Dean’s side as though for emphasis, eliciting a grunt of pain as he curled in on himself. “And haven’t you learned by now not to get in my way, Castiel?”

“I’m just following protocol,” he replied easily.

“Well, how about you respect seniority, instead? Unless you feel like finding a new job.”

“Break it up, boys,” a man with a gravelly British accent spoke from close behind Dean. “Alastair, the warden sent me to get you. He wants a word.”

“Is that so?” Alastair asked skeptically.

“It is. Something about a job offer. Castiel and I can take it from here.”

He let out an irritated huff as he brought the baton down on Dean once more. “I’ll be seeing you around, Winchester.”

Dean heard his retreating footsteps and he sagged in relief against the ground. The relief lasted until he cracked his eyes open and rolled onto his back to see Crowley standing over him. Well, this day just kept getting better.

“You really need to learn the proper way to intervene, Cassie,” Crowley advised.

“I was just-” Castiel started, but Crowley cut him off.

“About to lose your job. Now, let’s get these two to the infirmary. Get Fitzgerald, would you? I’ll take Winchester.”

“No, I’ll take him,” he protested. Dean caught the motion in his peripheral vision of Castiel starting to bend down before Crowley stepped over his body to block him.

“Careful,” Crowley said coldly. “I may not have the sway that Alastair has, but you’ll piss him off again, and I don’t have to save your ass next time.”

“I didn’t ask you to this time.”

“No. But between you and Alastair, I know who I dislike less. I advise you not to change that.” He turned around, looking down at Dean. “Can you get up?”

Dean nodded. He started to push himself up, but then everything started spinning again and he had to pause before he fell back to the ground.

“Okay, easy,” Crowley said soothingly as he reached down to help him up the rest of the way. He wrapped an arm around him, supporting most of his weight as they followed Castiel, who was carrying the little guy into the building.

“Are you okay, Dean?” Castiel asked over his shoulder.

“Been better,” Dean muttered. “Guess I didn’t do so well at avoiding Alastair’s attention, huh?”

Crowley scoffed. “Sorry to break it to you, but you never would have been able to.”

Castiel turned around with a frown that matched Dean’s. “What do you mean by that?”

“Dean here had a target painted on his back from the moment he walked through the prison doors. I suggest you ask your brother about the Winchesters – he’ll tell you the story. But for now, keep moving – the sooner we get him to the infirmary, the better.”

“What are you talking about?” Dean demanded when they started walking again.

Crowley sighed. “You should save your strength; the nurse won’t be kind to you. We can do story time once you’re better.”

“But-” Dean pulled away to get a better look at him, but that was a bad idea. A wave of nausea rolled over him and he froze.

“Dean?” When he didn’t respond, Crowley stepped around in front of him to look him in the eyes. “You alright?”

He didn’t want to open his mouth, so he just shook his head.

He nodded as though he had expected as much. “Alright, I’ve got you,” he said as he picked Dean up bridal-style and proceeded to carry him down the hallway.

Dean closed his eyes and let his head rest against Crowley’s arm. Maybe it was the fact that he was on the brink of going unconscious, but he was having trouble remembering why Crowley was as bad as Alastair. He was certainly preferring Crowley right now, and it didn’t hurt that he was good-looking with a great accent and could carry him in his arms with no problem. Seriously, why didn’t he want his attention, again? Dean slipped into unconsciousness with that question whirling in his mind.


	3. History Lesson

The first thing that Dean became aware of upon awakening was the pain – it was like someone was cutting into the side of his head. The second thing he became aware of was that someone was standing over him, and… wait, _was_ someone cutting into his head?

His eyes sprang open and he recoiled from the woman who stood beside the table he was laying on. “Who’re you?” he demanded.

She sighed as she glowered down at him through the frame of curly, brown hair. “Hi, I’m Meg, I’m a nurse.” She gestured to her scrubs to illustrate her point. “Now, I suggest you hold still, or else this needle just might end up in your eye.”

“Oh… right.” He forced himself to relax as the needle pierced his skin again. Of course, he was getting stitches – without any anesthetic, but he hadn’t really expected that any nurse that worked here would be kind enough to do anything to ease his pain. So, he gritted his teeth and did his best to endure the pain as Meg took her sweet time stitching him up.

“Where’s the little guy?” he asked when she was finally done.

She didn’t say anything, just nodded to the table on Dean’s left. Looking over, he saw that the guy was still out, but from the look of him, he should be okay. Good. At least he hadn’t taken this beating for nothing, then.

He turned back to Meg, who was cleaning things up. “So… what made you want to be a nurse at a prison?” he asked casually. He knew it was a long shot, but he was hoping that if he was nice and made some small talk, she might give him something for the pain.

She glanced back at him, her expression unreadable. “I fit in better with criminals. And I’m a daddy’s girl. He used to be a guard here.”

He arched an eyebrow, but quickly relaxed it as pain shot through his nerves. “Used to be?”

She turned back around to face him fully, her expression turning frostier by the second. “He got arrested.”

Huh. So, guards here did get arrested. Who knew? From the way they acted, he had figured that they were all above the law. So, what must her dad have done to actually have to face consequences for his actions? “What for?”

She sneered. “Because-”

“Meg,” Crowley called her name sharply as he entered the room. “I thought I told you to call me when Winchester was awake.”

She turned to him with a hateful glare. “I was about to.”

“I’m sure you were,” he said coolly.

She rolled her eyes. “Ever since my father’s arrest you’ve been acting like you’re a big-shot now. But guess what? You aren’t.”

Crowley’s expression didn’t waver as he took a step closer to her. “Really?” he asked softly. “Because I’m fairly certain that my ranking is above you, so when I tell you to call me as soon as a patient is ready to be returned to his cell, _I expect it to be done.”_

“And it was going to be done.”

He arched an eyebrow at her. “Really? Are you sure you weren’t going to call Alastair first so that you had somebody to hide behind?”

Oh, she was friends with Alastair. No wonder small talk hadn’t seemed to be going anywhere; there was absolutely no way she would be giving him any pain medicine if that was the kind of people she associated with.

Meg’s jaw clenched. “I don’t need to hide behind anyone.”

“Well, good for you, cupcake. I’ll just take Winchester and be out of your hair.”

She stared him down for a few more seconds, before she sighed and walked over to check on the little guy.

Crowley smirked and walked over to Dean. “You good to go, Dean?”

“Uh…” Dean looked up at him cautiously, wondering what the hell he wanted with him. Crowley had insisted on carrying him to the infirmary, and now he was going out of his way to pick him up. And from what Benny had told him about the guy, that wasn’t good. But it wasn’t like he could refuse to go with him – and he didn’t particularly want to stay here with Meg, either. “Yeah, I think,” he muttered as he slowly pushed himself up and got to his feet. He didn’t immediately drop to the ground, so that was a good sign.

“Excellent. Come with me.” He placed his hand on Dean’s lower back and led him into the hall.

Dean glanced down at Crowley’s arm as they walked, waiting for him to move his hand. He didn’t. The hand remained splayed against the thin fabric of Dean’s jumpsuit, and as much as he tried, he couldn’t ignore it. But something told him that slapping his hand away wouldn’t end well for him, so he pretended that it didn’t bother him.

“How are you feeling?” Crowley asked after several seconds of silence.

“I’m fine,” Dean muttered, not wanting to admit how much pain he was still in, especially to a guard he was ninety-percent sure he couldn’t trust.

He chuckled. “You put on a brave face, I’ll give you that.”

He chose to ignore that, instead asking, “So, what were you going on about before? How does Alastair know me?”

“Oh, darling, it’s not just Alastair. Nearly every guard in this place has a grudge against your family.”

Dean blinked in surprise. How the hell would any of the guards here know his family? His father had never been in prison, and it wasn’t like anyone in his family was well known. It didn’t make any sense. “Why?” he demanded.

Crowley looked at him thoughtfully out of the corner of his eyes before abruptly changing direction, ushering Dean down an empty hallway to their right. A few feet down it, he dropped his hand and pivoted to stand in front of Dean, seemingly assessing him. “What do you know about your mother’s death, Dean?”

Anger and suspicion flared in Dean at that. Crowley really had the nerve to stand there, acting like he knew more about his mom’s death than Dean did? He couldn’t, could he? “Some lunatic set fire to our house,” he snapped, all thoughts of being civil flying out the window.

Crowley didn’t seem to be offended, though; on the contrary, he looked amused. “That what your daddy told you?”

He had just enough self-control to resist punching him in the face. “It’s what happened,” he said through gritted teeth.

“True,” he agreed with a slight smirk. “But did he ever tell you that he caught the man who did it?”

He blinked in surprise. He didn’t want to believe him, that his dad would keep something like that from him, but why would he lie about this? “What?”

Crowley’s smirk grew. “Thought not. See, initially, there was no evidence to suggest it was anything other than an accident, but your dad knew better. The police wouldn’t help, so he pursued the case on his own. Eventually, he got enough evidence to put your mother’s murderer behind bars.”

Dean shook his head, staring at Crowely incredulously. “How do you know all this?”

“Because I knew her killer. Azazel. He was a guard here – worked here even longer than Alastair, and just like him, he more or less ran the place. Your mother was doing an outreach, or something of that nature here, and she caught his eye. Of course she turned him down, but Azazel doesn’t give up easily. He told her that if she didn’t leave your father for him, he’d kill her youngest son – the fire was set in your brother’s nursery, was it not?”

Dean’s breath left him in a huff as he turned to lean back against the wall, rubbing his hand over his face. Holy shit. The bastard had been trying to kill Sam. Even though he had been so young the night his mother had died, it was burned into his memory. She had been staying up in Sam’s room that night – Dean had thought nothing of it at the time, but she must have been worried that something would happen. The smell of smoke had woken both him and his father up, and his father had run into the burning nursery to save Sam just in time. Dean could clearly remember the feel of his baby brother in his arms when his father had passed him off to him and told him to get outside. Meanwhile, he went back for his wife, but it was too late. Dean blinked away the tears that were forming in his eyes, determined not to let Crowley see him cry.  

Crowley nodded, Dean’s reaction a good enough confirmation for him. “Azazel could have gotten away scathe-free, if it weren’t for your father. So, you see, the name ‘Winchester’ is rather infamous around here. Azazel was quite close to most of the guards – Alastair, especially. And you just met his daughter.”

Dean closed his eyes. Meg was his daughter. Damn. That explained why she got so pissed when he had started asking about her father. So, not only did most of the guards here hate him and want to punish him, so did the nurse. Great. Just great. “So, were you best-buddies with Azazel, too?” he muttered angirly as he opened his eyes and turned to look at him.

He raised his eyebrows slightly. “Me? No.” He shook his head in disgust. “I couldn’t stand him. He was always getting in my way – I was thrilled to see him gone. That’s why I’m telling you this, why I want to help you.”

Shit. Dean’s stomach dropped, his anger evaporating slightly, as he realized just what Crowley was playing at. “Help me?” he asked cautiously, though he already knew what was coming.

Crowley’s eyes were wide and honest, but Dean could also see in them the enjoyment he was getting from backing him into a corner like this. “You’re going to be a target, Dean; I can protect you.”

He shifted his stance away from the wall to face him more fully, crossing his arms over his chest. “I’ve never had any problems protecting myself,” he said coolly.

“Things are different here,” he protested, his expression taking on a slightly exasperated edge. “Alastair has already gotten his hands on you once. I can help make sure it doesn’t happen again.”

“And let me guess, you’ll want something in return.”

He smiled. “Naturally.”

 _‘Wait till you see what happens to those who don’t take him up on his deals,’_ Benny’s words echoed in his head. And he knew exactly what would happen to him – Crowley would stand back and watch as Alastair beat him to death. Well, at least that way he would die his own man and not live as Crowley’s bitch. “Thanks, but no thanks.”

Crowley’s expression shifted to disbelief. “Alastair _will_ kill you.”

Dean shrugged. “Well, I’m not really living in here, am I?”

“I could change that,” he offered.

“Nah, I’m good,” he said with a bitter smile.

Crowley’s jaw clenched, his eyes narrowing as all traces of genuinely caring for Dean’s wellbeing vanished from his face. “You won’t be smiling after a day in here without my protection.”

“Oh, I don’t know. I’m pretty good at smiling through pain. It’s pretty painful talking to you, but I’m smiling now, see?” His smile widened as he gestured to his face. He had already pissed Crowley off, so what the hell? It wasn’t like his situation could get any worse.

He ground his teeth together in irritation. “I think it’s time you go back to your cell.”

“Yeah, I think so. Because this –” He motioned between the two of them. “Isn’t going anywhere.”

He grabbed him roughly by the arm and practically drug him back to his cell. Benny looked up as he heard the cell being unlocked, and his eyes went wide as he saw Crowley.

“I suggest you reconsider my offer,” Crowley’s voice was positively venomous as he threw Dean into the cell.

Dean just managed to catch his balance before he fell on his face, and he turned around to meet Crowley’s gaze levelly. “Not a chance.”

They stared each other down for a second, before Crowley turned around and stalked off, Dean’s cocky composure dropping as soon as he was out of sight.

Benny whistled and Dean turned around to face him. “You turned Crowley down?”

“Yep,” he sighed, leaning back against the cell door as the weight of everything he had just learned crashed down on him.

“You must be mad. He’s goin’ to make your life Hell.”

He shook his head. “No, he won’t.” Of that he was sure.

Benny arched an eyebrow at him. “I know you took quite the beating, but I didn’t think it was enough to knock all sense out of you.”

Dean scoffed. “He doesn’t have to do anything to me,” he explained. “Alastair will take care of that for him – along with every other guard in this place.”

He frowned slightly. “I’ll take it there’s somethin’ I don’t know here.”

Dean grinned bitterly as he walked over to sit down on his bed. “Yeah. I didn’t know it either until five minutes ago.” He took a deep breath. “Apparently, a former guard killed my mom, and my dad was who found enough evidence to get him arrested. And I guess the guy was Alastair’s best friend, along with being buddies with pretty much every other guard, and the father of the nurse. So, they all hate me.” He let out a hollow laugh. “Crowley offered to protect me, but… there are some levels I’m not willing to stoop to.”

“Damn,” Benny sighed as he sat down next to him, looking at him in disbelief. “You are a special kind of crazy, Dean.”

“Yeah, guess so,” he muttered. He knew he had to be crazy to turn down Crowley’s offer, but that knowledge wasn’t enough to make him reconsider. “How screwed am I?”

“Completely.” He turned slightly on the bed to angle himself towards him, his gaze thoughtful. “I think you could use a distraction.”

Before Dean could wonder what he meant by that, he cupped his cheek in his hand and leaned in to press his lips against his. Dean froze for a second before returning the kiss hesitantly, his hand coming up to rest on his back. Benny took that as encouragement, deepening the kiss as he gently pushed Dean down onto the bed.

Dean knew that if he didn’t stop this now, he would lose all willpower to do so, but he couldn’t think of a good enough reason to. He liked Benny, he was enjoying kissing him, and from the looks of things, he was going to die in this prison, so he might as well have some fun while he was there.


	4. Under the Radar

Dean didn’t want to open his eyes, finding it easier to pretend that he was still asleep. He had been with his fair share of men and women, and on the rare occasions that sleeping together had led to _sleeping_ together, he had always politely, but quickly excused himself the next morning – relationships just weren’t his thing, especially not when his number one priority was being there for his family. So, given that he was waking up in bed with his cell mate that he couldn’t exactly get away from, he was feeling a little out of his element.

He couldn’t lay there forever, though; so, he ignored the knot in his stomach as he opened his eyes and turned his head to peek behind him at the man spooning him.

“Mornin’, sunshine,” Benny purred when he saw that he was awake.

“Uh… morning…” Dean muttered, the other man’s arms falling away from him as he sat up, running a hand over his face.

“Was I reading things wrong last night?” he asked after a few seconds of silence. “Or do you always look conflicted the morning after?”

He chuckled half-heartedly. “No, you weren’t reading things wrong. I just… I’m not used to being stuck in close quarters with someone after a one-night stand.”

“Hmm…” Benny hummed thoughtfully as he traced his fingers up the skin of Dean’s back. “Well, who said it had to be a one-night stand?”

Crap. Dean rose to his feet, rubbing his hand over the back of his neck uncomfortably as he turned to look down at Benny. “Look, man, I like you and all, but-”

“Woah, slow down, brother,” he laughed. “I’m not interested in anything serious, either, but it don’t have to be all or nothin’. You ever heard of friends with benefits?”

It took a second for that to sink in, and then Dean almost laughed with relief, feeling a little ridiculous for how worried he had been. “Oh. Um, yeah, that… could be nice,” he agreed with a small smile.

“Thought you might think so.” He got to his feet and started getting dressed, Dean following suit. “Anyone ever tell you you’re a pretty open book during sex?”

“Once or twice,” he admitted with a shrug. He knew that his pleasure was always written plainly across his face, and on top of that, he was normally quite vocal, but he saw no reason to be ashamed. Why should he hide how much he was enjoying himself?

“Though, I suppose…” Benny mused thoughtfully as he turned back to face him. “Dating you wouldn’t be much of a commitment with your projected life span.”

Dean scoffed. “Guess you have a point there.”

He frowned slightly. “You sure you don’t want to reconsider Crowley’s offer? I mean, the guy’s scum, no doubt about it, but he can keep you alive.”

“Yeah, at what cost, though?”

“Did you let him talk long enough to find out?” Benny shot back at him, his tone taking on a slightly amused hint.

“No,” he admitted. “But it ain’t gonna be anything good.”

“It’s got to be better than being beaten to death by Alastair.”

Dean sighed. “I just… I’ve lost everything, and the only thing I have left is my pride – and I am _not_ letting Crowley take that from me. He doesn’t get to control me.”

Benny looked at him thoughtfully for several seconds. “Anyone ever tell you that pride’s a sin?”

He snorted. “So is murder, but I ain’t losing any sleep over it.”

He chuckled. “Guess you got a point there. Still think you’re crazy, though.”

“Hey, clearly you have a thing for crazy,” Dean pointed out with a wink.

He rolled his eyes. “Clearly I have a weak spot for a pretty face that could end up getting me into trouble.”

Dean paused, his amused expression fading to concern. He had a point– it sounded like Benny had been pretty lucky to escape guards like Alastair’s attention so far, but if they found out that he and Dean were more than just cell mates… “Hey, if you want to distance yourself-”

Benny held up his hand, interrupting him. “Nah, I’m good,” he assured, the corner of his lips twitching up.

“You sure?” he checked, arching an eyebrow at him. “I mean, I won’t blame you for getting out of the crosshairs.”

He shrugged. “I’ll take my chances.”

Dean grinned, honestly a bit relieved. He hadn’t been too keen on the idea of navigating prison life on his own. Sure, he could do it, but when everything sucked, it was nice to have at least one good thing – or in this case, person – to help support him through it all. He just hoped that Benny wouldn’t regret his decision.

If Dean stopped to think about it, he’d probably realize that Benny standing by him was a good thing in more ways than the one. He had never been terribly cautious about putting his own life at risk – and the way he saw it, there was already a target painted on his back, so what was the point of keeping his head down and playing nice? Except for that he wouldn’t put it past Alastair and some of these other guards to hurt those close to Dean just so he’d have it on his conscious. Or if they did go straight for their target, they may go on to beat on whoever was in closest proximity to him while they were at it, because why stop at one? If it weren’t for Benny’s sake, Dean would see no sense in trying to protect himself, but he couldn’t let Benny get hurt for him, so he did his best to avoid drawing attention to himself, as well as to his relationship with his cell mate.

It was for that reason that he decided to distance himself from Benny during free time that day. It wouldn’t turn too many heads for him to eat meals with his cell mate, but if he spent too much time with him, surely someone would realize they were friends.

He scanned the yard and caught sight of the little guy that he’d intervened for the previous day. He had a black eye, but he was up and walking around, so he couldn’t be doing too bad.

“Hey,” Dean greeted him as he approached.

He turned to him with a smile. “Hi,” he replied, his voice surprisingly friendly.

“How’re you doing? You took quite a hit yesterday.”

“Oh, I’m fine. I’m resilient. Wait – they told me someone stepped in to help me – was that you?”

“Uh, yeah,” he admitted with a shrug. “I’m Dean.” He offered out his hand.

Instead of shaking his hand, the other guy opted to pull him into a hug, instead. Dean blinked in surprise, returning the hug awkwardly.

“I’m Garth,” the guy supplied as he pulled away.

“Okay. Uh… don’t take this the wrong way, but you don’t really seem like a hardened criminal.”

“Oh, I’m not. I was framed,” he explained, his expression falling slightly. “Some of my in-laws were up to a lot of bad stuff, and when they caught the law’s attention, they managed to pin it all on me.”

“Man, that sucks,” Dean sighed sympathetically.

“Yeah…. My Bess believes me, though, and I have full faith in her that she’ll find evidence to clear my name.”

“Well, I wish you luck. You seem like a nice guy.” Far too nice to last long in this place, that was for sure.

“Thank you, Dean. You too.”

“Winchester.” Dean’s blood ran cold as he heard the sharp bark of a guard’s voice. He swallowed thickly as he turned around to see Gabriel walking up to him. “You got a couple of visitors.”

“Oh. Okay.” Surely that was the truth, right? Gabriel was supposed to be one of the better guards – he was Castiel’s brother – he wasn’t someone he had to worry about. Still, Dean felt had he had good reason to be cautious. He glanced back at Garth. “Well, it was nice meeting you.”

“You too, Dean. And thanks for yesterday.”

“No problem.” Okay, it might have caused a few problems, but he didn’t need to know that. He nodded goodbye, then turned to follow after Gabriel, hoping that he wasn’t in for a nasty surprise. But even if he was, at least it didn’t look like anyone else would be hurt alongside him.

“Cas told me what happened yesterday,” Gabriel said as they entered the building. “I’m assuming Crowley explained?”

“That most of the guards here want to crack my head on the pavement all because my dad caught the man who murdered my mom? Yeah, he explained.”

He chuckled. “You’ve got spunk, kid. I admire that. But you should really be careful who you run that mouth around.”

“Tell me, do you really think that will help me any?” Dean challenged.

He looked at him thoughtfully, smirking slightly. “Suppose not. Do me a favor, though?”

He crossed his arms over his chest and arched an eyebrow at him, silently indicating for him to continue.

“Try to keep your head down when my brother’s around. He likes to play hero and doesn’t know when to stop.”

“And he’s close enough to being fired, as it is,” Dean finished for him with a nod. “Alright, I’ll do my best.” It was starting to look like, between Benny and Castiel, he might actually be keeping his head down consistently.

“Thank you.”

Gabriel led him into the visiting booths and he felt a real, genuine smile spread across his face as he sat down to see his father and brother on the other side of the glass. He picked up the phone to talk to them. “He-”

He wasn’t even able to finish the word before his dad interrupted him sharply. “What happened?”

Right – his face was bound to still be messed up from his altercation with Alastair. The altercation that his dad had to have known was coming. Dean’s joy evaporated slightly as he looked down, wondering why he had been kept in the dark. “I think you know,” he said quietly.

John sighed, while Sam looked incredulously between the two of them. “What the hell is that supposed to mean?” he demanded, the question clearly more directed at their father.

“It’s a long story,” John said reluctantly.

“A long story that got Dean beat up? It sure sounds like one we deserve to hear.”

John didn’t respond, instead making eye-contact with his eldest son. “How much do you know?”

“Enough,” Dean answered, following his lead to not say anything in front of Sam. At least for now – his dad had to have some reason to keep them in the dark, and if it had anything to do with Sam’s safety, he’d help keep his secret. “Still don’t get why you never told us.”

“Never told us _what?”_ Sam was now glaring at them both. Dean felt bad, but not bad enough to cave.

“Never mind, Sam,” John said firmly. “I did some things I’m not proud of. I’m afraid it made me some enemies that now have access to Dean. I’m sorry, son – I was hoping they wouldn’t target you.”

“Yeah, I know.” Dean didn’t blame him for the position he was in, there was nothing he could have done about it. “But… what do you mean, not proud of? Seems like a good thing to me.”

He smiled grimly. “The end result was, yes. But to get the information I needed… well, it wasn’t easy.”

He burned with curiosity, but he knew better than to ask. Even if his dad would tell him, he couldn’t do so here, in front of Sam and where any guard could find out what he said. “It was worth it,” he said instead.

“Not if you have to suffer for it.”

Sam, who had been stewing silently while they talked, had clearly had enough. _“Dean,_ what’s going on?”

Dean sighed. “It’s nothing you need to worry about, Sammy,” he said soothingly.

“Bullshit. You’re hurt, and apparently it has something to do with something Dad’s been keeping from us. Are you really going to help him keep his secret when it’s what made you look like that?”

“Yes. Because he has his reasons for not telling us. And what do you mean made me look like this? I look fantastic.”

“Dean, this isn’t funny,” Sam sighed in exasperation.

“No, it’s not,” John agreed. “But this conversation is over. You can either continue arguing, or you can enjoy the time we have to talk to Dean.”

He glared at him for a few more seconds before his shoulders slumped in defeat. “Fine.”

The rest of the conversation passed without any mention of Dean’s injuries or their father’s secret; though, from Sam’s expressions, it was clear he wasn’t done trying to get answers. Sam was stubborn that way, but so was their dad, and Dean knew his brother wouldn’t be getting the answers he wanted. It was for the best, really – he didn’t need to know that the fire was intentional, and that he was the intended target. He already had to live with the fact that he never knew his mom, he didn’t need to blame himself for her death, too.


	5. Interrogation

Dean was lucky enough to avoid Alastair for the next week. Sure, there were some other guards that hit him around a bit, but he knew it could be a lot worse. He was confident that his lucky streak wouldn’t last long, though; Alastair would catch up to him sooner rather than later.

“It really is a pity,” an immediately recognizable voice interrupted Dean as he loaded clothes into the washer. He spun around to glare at where Crowley was standing in the doorway. “That a face as pretty as your will be marred by Alastair,” he continued.

Dean shifted uncomfortably, his gaze darting away from the guard in front of him. He wanted to be disgusted by the comment, but the fact was that a large part of him wasn’t sure that he’d have to good sense to turn Crowley down if he made a different kind of offer. “Go to hell,” he muttered, turning back to his work.

Crowley chuckled as he walked forward until he was close enough to curl his hand around Dean’s wrist, stopping him.

He took a deep breath as he looked up at him, making sure that his glare didn’t waver. “Something I can do for you?” he demanded coolly.

He smirked. “Oh, I can think of a few things. Unfortunately, we don’t have the time. I happened to catch wind that Alastair is on his way to pay you a little visit.”

He set his jaw, determined to not let the fear that knowledge gave him show on his face. “That so?” he asked, keeping his voice carefully void of emotion.

Crowley took another step forward, now standing so close that Dean could feel the warmth radiating from his body. “I could move you to a different job,” he offered in a low voice that promised far more than the words he said.

Dean licked his lips. Shit, now he was _trying_ to get him flustered. He took a deep breath and took a deliberate step back from him, pulling his wrist out of his grasp. “No, thanks. I’m good.”

He sighed. “Dean, I sincerely _want_ to help you here. Just hear me out.”

He rolled his eyes. “The only thing you _sincerely want_ is whatever it is you’re trying to get from me.”

“That’s not true,” Crowley protested, and Dean raised an eyebrow skeptically. “That’s only one of the things I want. I would also like to ruin Alastair’s fun, and believe it or not, I would prefer you in one piece.”

“Well, get used to disappointment.”

He sighed. “I don’t do disappointment. You’ll come around.”

“Don’t count on it.” He met Crowley’s confident gaze with an equal amount of determination. Once he set his mind to something, he didn’t back down.

They stayed like that for a couple of seconds, until they heard someone clear his throat in the doorway. A sense of dread flowed through Dean as he tore his gaze away from Crowley and turned his attention to Alastair.

“Crowley,” Alastair spoke in his dry, grating voice that made Dean wonder how anyone who heard it didn’t automatically know that this guy was pure evil. “Would you be so kind as to give me a minute with Mr. Winchester, here?”

Crowley arched an eyebrow at Dean, clearly giving him one last chance to take him up on his offer, but Dean ignored him. Yeah, this was going to suck, but the only freedom he had left was that of free will, and he wasn’t going to let Crowley take that from him.

“Of course,” Crowley said smoothly. His gaze remained fixed on Dean for a couple seconds after he spoke, then he turned and walked for the door. He slowed as he approached Alastair, turning to him with a smile. “I’ll ensure you’re not interrupted.”

Alastair returned his smile. “Appreciate it.”

He tilted his head to him, then left the room, leaving Dean alone with Alastair.

There were a few seconds of silence, in which Dean watched the guard apprehensively, while Alastair smiled at him. It was almost a relief when he began to approach him. “I didn’t get the chance to properly introduce myself the other day.”

“Don’t bother,” Dean said, the last of his sense of self-preservation flying out the window. “I know exactly who you are.”

“Is that so?” he asked, vague amusement in his voice.

“Oh, yeah. See, at first, I thought you were top dog here – the man that no prisoner dared to cross. But then I realized… you’re just the lackey of the asshole who murdered my mom.” He grinned bitterly as the smile was wiped from Alastair’s face.

“I’ve found in the past,” he mused thoughtfully as he strolled forward. “That those who like to crack jokes, don’t generally keep it up for long.”

Dean refused to back down. “Oh, I ain’t joking. Just stating a fact.”

“Call it what you will, but I can promise you, it won’t last.” He grabbed hold of Dean’s wrist, twisting his arm to the point that it felt it was about to break.

Dean knew better than to fight back, so he gritted his teeth against the pain, glaring at the man in front of him.

“Tell me,” Alastair continued. “Did your daddy ever tell you where he got his information?”

Dean blinked in surprised. “What?” he asked in bewilderment.

He sighed impatiently. “The information that convicted Azazel. _Where did he get it?”_

He stared at him in disbelief. So, this wasn’t just about getting revenge against his father, this was about getting information. Not that it made much of a difference, though, considering that Dean had nothing to tell him. “Dude, sorry to break it to you, but you’re wasting your time. I don’t know.”

“Really?” Alastair applied more pressure and Dean couldn’t suppress the shout of pain that covered the snap of his wrist breaking. “I suggest you think harder.”

“I suggest you go to hell,” he spat through clenched teeth.

To Dean’s horror, he continued twisting his wrist. The sick bastard was even smiling, as though this was the most fun he’d had all year.

“I don’t know!” he panted through the pain. “Dad never told me.”

Alastair searched his face for a minute before releasing his grip on his wrist. Dean breathed a sigh of relief as he brought it up to cradle in his other hand.

“Well, I’d say you’re telling the truth,” Alastair decided. “So, I’m going to give you some time to think. Try to remember what your father did in the time between your mother’s death and catching Azazel – the places he went, people he spoke to, names he might have mentioned in passing. If you can give me information, I might take it easy on you.”

 _Yeah, I doubt that._ But it would be in his best interests to play along, for the time being. It would get him a reprieve, at the very least. “Fine,” he muttered.

“Good. Now, let’s get you to the infirmary.”

Dean wasn’t at all surprised at Meg’s lack of gentleness as she tended to his broken wrist, but at least it was Castiel that showed up to escort him back to his cell that evening.

“I somehow doubt that you broke your wrist while loading laundry,” Castiel commented as they walked. That was the story that Alastair had told Meg to write down for the record, and while Dean knew that no one would believe it, he also knew that it didn’t make any difference.

“Yeah, it doesn’t take a genius to figure that out,” Dean muttered. “It’s fine, though,” he added, remembering his promise to Gabriel. “Don’t worry about it.”

He frowned at him. “It was Alastair, wasn’t it?”

“Yeah,” he sighed. “But it could’ve been worse.” He knew full well that he’d gotten off easy this time.

“The severity of the injury does not lesson the crime. Alastair should not be able to get away with the things he does.”

“Yeah, but it’s just the way this place is.” Dean shrugged. “And there’s no use you getting into trouble trying to change that, when you know it won’t do any good.”

“I appreciate your concern, Dean, but whatever action I take is my own choice.”

“I don’t want you getting fired over me. Me being in here is causing enough hardship, as it is.”

Castiel stopped, turning to face Dean as his frown deepened. “What do you mean?”

He sighed. He hadn’t thought much about the words when he’d been saying them, but now that they were out there, he felt embarrassed. “I’m just… worried about my family,” he muttered, looking at the floor. “My dad doesn’t make a lot, and I always worked a crap ton of overtime to make sure we had enough. They told me they’re doing okay when they came to see me, but… they’d say that no matter what state they’re in.”

Castiel reached out to place his hand on Dean’s shoulder. “I am sure that your family will find a way to make do. And if it is any consolation, I will keep them in my prayers.”

Dean resisted the urge to roll his eyes. He’d never been much of a believer after all the crap his family had been through, but he didn’t want to mock Castiel’s faith. He appreciated the sentiment, all the same. “Thanks.”

“You’re welcome,” he said with a soft smile, before he continued walking, Dean falling into step beside him.

“You really should let this thing with Alastair go,” Dean continued. “This prison is lucky to have a guard like you. I can’t imagine what it’d be like with you gone. You can do far more good keeping your head down and doing little things than you could do if you made noise and got fired.”

Castiel was silent for a few seconds as he mulled that over. “I suppose you are right,” he finally admitted. “I just don’t like standing by and doing nothing.”

“Yeah, I know that feeling. Got into a fair amount of fights because of that.”

“And if you could go back, would you do things any differently?”

“Hell no,” he chuckled. “But that doesn’t mean I shouldn’t. I’m not known for making the best decisions – clearly. And I was also never giving up being one of the only decent human beings the people in the place get to interact with.”

Castiel looked at him with a smile. “Has anyone ever told you that you are very wise, Dean?”

He burst out laughing. “No. No, I have definitely never been told that before.”

“Well, you seem quite wise to me.”

Dean arched an eyebrow at him. “Explain to me why I’m in prison, then.”

“Because you do not listen to your own wisdom.”

He shrugged. Castiel might actually have a point, there. “That mean you’re going to?”

“I will do my best,” he sighed as they approached Dean’s cell. He opened the door, and Dean walked inside. “Goodnight, Dean.”

“Night, Cas.”

Dean heard the sound of Benny jumping down from his bed as the cell door was shut, and he turned to face him as Castiel walked away.

“So?” Benny asked, motioning towards Dean’s wrist. “Who was it this time?”

“Alastair,” Dean sighed as he walked over to sit on his bed.

He frowned down at him, leaning against the bedpost. “Well, we knew that was comin’ at some point. Still, he left you in better shape than most.”

He scoffed. “Yeah. Apparently, my pain isn’t all that he wants from me. He wants information. Thought that if he scared me enough I’d be able to come up with something.”

Benny’s eyebrows furrowed. “What information?”

“I guess he figures that someone told my dad what he needed to know to get Azazel convicted,” he said with a shrug.

“And he thinks you know who it was?”

Dean shook his head. “Nah. I convinced him of that much, at least. But he thinks I might have seen or heard something that could point him in the right direction. The problem is, Dad didn’t even tell me Mom’s death was murder – he certainly didn’t give me the chance to learn anything about the case he was building against her murderer.”

The corner of Benny’s mouth quirked up. “Even if he had, would you tell any of it to Alastair?”

“Hell no. But I don’t know anything, so it doesn’t matter.”

“So, what does that mean for you?” he asked, concern working its way back into his expression.

“That I’d better make the most of this reprieve,” Dean sighed. “Because things won’t be good once it’s over.”

He could tell that Benny was on the verge of saying something, but he seemed to think better of it – he’d probably been about to try to get him to take Crowley up on his offer, again. “Suppose I should let you get your sleep tonight, huh?” he asked instead, his eyes dancing mischievously. “You probably won’t be able to do much with that wrist, anyway.”

His eyes narrowed. “Shut up and get down here.”

Benny smirked as he leaned down for a kiss, and Dean used his good hand to pull him onto the bed. At least he could have this one good thing today.


	6. Family Ties

Dean couldn’t stop wondering how long Alastair would give him before laying into him again. A day? A week? He knew full well that Alastair wouldn’t be going as easy on him the next time around, and he was dreading it. If he wasn’t so stubborn, he might actually consider taking Crowley up on his offer, but as it was, he quashed the idea as soon as it entered his mind. He wasn’t going there.

Whenever he was working, he kept waiting for Alastair to walk into the room. He was actually relieved when another guard came in and started beating on him. Brady wasn’t as tough as he thought he was, but that didn’t matter when he applied pressure to Dean’s broken wrist. He had remained resolutely silent, determine not to give Brady the satisfaction, but when the pain flared in his wrist, he couldn’t suppress the grunt of pain.

“I think that’s enough, don’t you, Brady?” Dean looked up to see Gabriel standing in the doorway. “Or do you want me to tell Lucifer that you’re not at your station?”

Brady narrowed his eyes slightly, but left without argument.

“Thanks,” Dean muttered as soon as he was alone with Gabriel.

“No problem.” He walked further into the room, looking over Dean. “You okay? Need to go to the infirmary?”

He shook his head. “He didn’t do too much damage – Meg would only make it worse.”

Gabriel chuckled. “You’re probably right about that.”

Dean returned to loading the washer, but looked back over his shoulder curiously. “So, would going to Lucifer actually have done any good? I was under the impression that the warden didn’t care what went on here.”

He shrugged. “You never know. I can sometimes get him to listen to me.”

“How do you mange that?” he wondered aloud. From what he had heard from Benny, Lucifer just sat back and enjoyed the chaos that the guards created, letting Alastair do all the dirty work.

The corner of Gabriel’s lips quirked up in a slightly bitter smile. “He’s my brother.”

Dean stopped what he was doing and spun around, his eyes widening in disbelief. “Your…?” If he was Lucifer’s brother, then so was Castiel. How could the only two decent guards in this place be related to the warden of this hellhole? “How?”

“Well, you see, our parents had sex multiple times, and-”

“Okay, I know _how!”_ Dean interrupted. “I just don’t get how you and Cas could possibly be related to him.”

“You’ve never even met him.”

“He runs this place. Are you saying he’s a decent guy?” he asked incredulously.

“I’m saying he’s my brother,” Gabriel snapped.

Silence stretched between them, and Dean could feel his cheeks heating up slightly. “Sorry,” he muttered as he turned back to the pile of dirty towels.

He sighed. “Don’t be. You’re right. I love him, but he’s a great big bag of dicks.”

“Got some family problems, huh?” Dean knew it wasn’t his place to press the matter, but he couldn’t help it, he was curious as to what the dynamic could possibly between Gabriel, Castiel, and Lucifer.

Gabriel scoffed. “You have no idea. Family dinners are like the apocalypse. Lucy and Dad can’t play nice for five seconds.”

He chuckled slightly. “Yeah, I know what that’s like. Sam and our dad can be like that, too.”

“I highly doubt it’s as bad.”

“From what I know about your brother, no, probably not,” Dean admitted, shaking his head slightly. “Wait. Cas is in danger of getting fired, right? Lucifer would seriously fire his own brother?”

“That’s the thing,” Gabriel sighed. “Lucifer had a falling out with the family when he took over the prison from Pops. This used to be a decent place, believe it or not. My oldest brother, Michael, had wanted to take over when Dad retired, but Lucifer went behind everyone’s back to get his name on the paperwork – I’m not entirely sure how he pulled it off, but he thought Dad was too soft on the prisoners, and he wanted to do everything in his power to change that. Michael was furious, Raphael took his side, and I was caught in the middle…. Castiel was too young to really understand what was going on, so he grew up only knowing this side of Lucifer – he refuses to even acknowledge him as his brother, and Lucy follows his lead. Really, I’m the only one of my brothers that still considers Lucifer family.”

“Uh, no offense, but _why_ do you still consider him family?” he asked tentatively. “I mean, he betrayed your whole family, from the sound of it.”

“Because I still remember what he was like before all of this,” he said, a touch of sadness in his tone.

Dean sighed. “I’m sorry, man.”

“Me too. I hate seeing what he’s done to this place. Sometimes I want to leave, but honestly, I don’t see Cassie lasting too long without me.”

He nodded, understanding dawning on him. “And that why Cas is so determined to fix this prison – because it’s his brother that made it like this.”

“Yep. Personally, I’d rather give up on a lost cause, but he’s stubborn.”

“And I thought my family had its problems.” Dean shook his head. “Hey, don’t suppose there’s any chance you could convince your brother to get the guards to lay off me a bit?”

Gabriel grimaced. “Lucifer will choose his favorites over his family in a heartbeat. His favorites, of course, being Azazel, Alastair-”

“Crowley. Yeah, I get it,” he muttered bitterly as he wadded up a towel and threw it into the washer. Everyone in this place was against him.

“Actually, I wouldn’t say Crowley’s a favorite. I mean, he’s up there, sure, but Lucifer’s wary of him.” He smirked. “And with good reason, too.”

Dean frowned back at him. “What do you mean?”

Gabriel glanced around before stepping closer to him and saying in a low voice. “Crowley’s after his job.”

Dean blinked in surprise. “What?” He wondered vaguely if the prison would be in better shape with Crowley running it, or worse. “How do you know?”

“Look, I know that Crowley’s not the most upstanding guy in the world, but a guy’s got to have a friend at work other than his brother. And he’s got a good sense of humor.”

Damn, Dean was learning a lot about one of his favorite guards. Not only did he have an evil bastard for a brother, but for a friend, as well. “And he just told you that he wants your brother’s job?”

Gabriel chuckled. “No, but I was able to piece it together. Not that I’d react badly. He wouldn’t be worse than Lucifer.”

That was debatable. “Well, I think you or Cas should run the place.”

He shook his head. “Not my kind of thing. And Cas… well, Crowley has a much better shot of getting the job. Now, keep your mouth shut about that, okay? No one needs that rumor getting out. I know how he can come across, but trust me, he’s better than Lucifer.”

Dean wasn’t sure he believed that. Sure, Lucifer was who was responsible for this place being the hell that it was, but there was something about Crowley that made him seem more dangerous to Dean. Maybe it was that he had no idea what his end-game was, or than he was so damn alluring. Either way, he didn’t trust him, and nothing that Gabriel said would change that. Still, he liked Gabriel, so for his sake, he wouldn’t go around spreading the word that Crowley was trying to become warden.

He did, however, tell Benny that Lucifer was Gabriel and Castiel’s brother during free time that day.

Benny let out a low whistle. “Now that I did not see comin’.”

“Tell me about it.” Dean shook his head.

“I always did wonder why Castiel worked here.”

“Yeah. Now we know it’s because he’s trying to clean up after his brother. And here I was thinking he just liked a challenge.”

Benny nodded over his shoulder. “Incoming.”

Dean turned around to see Castiel approaching him. “Hey, Cas,” he greeted him.

“Hello, Dean.” He inclined his head towards him with a small smile. “You have visitors.”

He found himself smiling. He tried not to spend much time dwelling on it, but he really missed his family. He nodded goodbye to Benny, then followed the guard.

“How are you faring, Dean?” Castiel asked once they were inside the building.

Dean shrugged. “Been better. Could be worse. How’re your attempts to kick this place into shape?”

He sighed. “As well as ever.”

“Kinda figured.”

“All I can do is hope that the little good that I can do goes some way in improving the life of at least some of the prisoners.”

“I’m sure that it does,” Dean assured him. He figured it was best to not bring up Lucifer. From the way Gabriel had made things sound, Castiel probably wouldn’t be too game for talking about him. So, instead he followed in silence to the visiting room, where his dad and Sam were waiting for him on the other side of the glass.

The conversation started off a lot less tense than it had on their last visit. His dad did ask about his wrist, but he brushed it off and changed the subject before it could turn into anything.

“Dean, I need you to be honest about something,” John started after they had been talking for a little while. “Have you arranged for anyone to send us money?”

Dean’s eyebrows drew together slightly. “I mean, I’ve been having what I make sent to you-”

“No, this is more than that.”

He frowned slightly, shaking his head. “Well, it’s nothing to do with me.” A suspicion nagged at the back of his mind, but he chose to ignore it for now. “You know what they say, though – don’t look a gift horse in the mouth.”

“I just don’t get why someone would just give us money if you didn’t put them up to it.”

He shrugged. “Dunno what to tell you.”

“You know, there are just decent people out there,” Sam pointed out. “People who do nice things without having to have some complicated reasoning behind it.”

“Kid’s got a point,” Dean agreed with a slight smirk, earning him a glare from his little brother. He winked at him. Just because he was in prison, it didn’t mean he had to neglect his big brother duty of giving Sam a hard time.

Castiel cleared his throat as he walked up behind Dean. “I’m sorry, but visiting hours are almost over.”

Dean nodded. “We’ll wrap it up.”

“Dad, can I talk to Dean privately?” Sam asked as Castiel walked away again.

John hesitated, but then sighed, “Sure. Be good, Dean. I’ll see you again soon.”

“Seeya, Dad.” He watched his dad get up and leave the room before his gaze returned to his brother. “What’d ya want to talk about, Sammy?”

“What’s dad not telling me?” he demanded bluntly. “What did he do that you now have to take the heat for?”

Dean sighed. He should’ve known that was what this was about. “Believe me, you’re better off not knowing.”

“No, I’m not!” he protested hotly. “You didn’t know, and now look at you!”

“This would have happened whether I knew or not. Besides, it won’t affect you.”

“How can you know that? Dad thought it wouldn’t affect you!”

“But you’re not going to end up in prison!” He shook his head. “Dad’s right about keeping this from you.”

“Are you saying that because it’s true, or because you always have to take his side on things?” Sam challenged.

“Because it’s the truth,” he said firmly. “You don’t need to live with this.”

“Isn’t that my choice?”

“No,” Dean answered immediately.

Sam sighed exasperatedly. “I’m not a kid anymore, Dean! I can handle it, whatever it is.”

“I know you can. But that doesn’t mean you should have to.”

“Dean,” Castiel’s voice drowned out whatever Sam’s reply was going to be. “I’m sorry, but you need to say goodbye.”

Dean grimaced. He hated leaving things on this note, but it wasn’t like he had a choice. “I gotta go, Sammy. I’m sorry, really.”

“Yeah,” Sam sighed skeptically. “Bye, Dean.”

“See you soon.” He watched sadly as Sam hung up the phone and left. And he had thought their fights at home had been bad – at least then they had had the capability of seeing each other to patch things up in the following days.

“I’m sorry,” Castiel said as Dean walked over to him. “I know fighting with brothers is hard.”

 _Yeah, I bet you do,_ he thought to himself. “Yeah,” he sighed. “I wish he would just listen to Dad for once.”

“They don’t get along?” he asked as they walked.

“Only about 10% of the time.” He hesitated. “Hey, um, can I ask you something?”

“Of course.”

He tried to figure out how best to say it. “You’re not – I mean, someone’s been sending my family money…. That’s not you, right?”

Castiel’s cheeks took on a faintly pink tinge and he looked away. “I had been hoping you would not figure it out. I didn’t want to make a big deal out of it.”

Dean shrugged. “There’s not a whole lot of options of people it could be…. Why, though?”

“Your family has been through a lot of hardship. I would like to help lessen the burden.”

He smiled faintly. “Thank you,” he said fervently. From the way things were looking, he was going to end up dying in this prison, so it was good to know there was someone out there looking out for his family.


	7. Break Out

Two weeks. That was how long Alastair gave him. Then he pulled him aside as he was leaving the cafeteria and ushered him into a storage room.

“Now, let’s try this again.” Venom permeated his words, and his smile was like a snake’s before it devoured a mouse. “Who was your daddy’s source? Think carefully! It’s your last chance, now.”

Well, he was screwed one way or the other, so he might as well piss him off. At least then he might end up getting knocked out sooner – better than suffering through whatever Alastair was planning to do to him. “Your mom,” Dean answered smoothly with a smirk.

Alastair’s eyes narrowed, but his smile grew wider, an excited glint in his eyes. Shit.

Suffice to say, Dean’s plan to get knocked out early to avoid prolonged pain didn’t go over too well, but to say that he wished it had was an understatement. He tried a few more times to get under Alastair’s skin, but nothing fazed him – no matter the severity of the insults thrown at him, he was perfectly content taking his time, drawing out the pain as long as possible. And all the while, he never stopped smiling. Maybe he had wanted that information, but Dean had a suspicion that he was happier with this turn of events.

He was pretty sure that Alastair must have done some research into all the best ways to inflict pain on the human body because there was something decidedly calculated about his actions. And the severity of the pain also went a way to support that theory. Dean eventually blacked out, not the force of the trauma, but from the pain itself.

He came to again in the infirmary. The first thing he registered was that he was still alive, which he found genuinely surprising. For a while there, he had been sure that he was dying. The second thing he noticed was Meg and Crowley arguing by the door.

“He’s in prison for life,” Crowley was saying haughtily.

“You underestimate him,” Meg spat. “He’ll get out.”

“No, he won’t. Your father will die in that prison, and it’s just what he deserves.”

“Because you’re _so_ much better than him?” she sneered.

“I am.”

“Well, he didn’t kill my mom, so he has that going for him,” Dean muttered.

They both turned towards him, and Crowley’s lips curled up slightly in an amused smile. “So, you’re awake,” he observed as he walked closer to the bed Dean was laid out on. “And saying nice things about me. I knew Meg was a rubbish nurse – she said you didn’t have any head trauma.”

Maybe he was still a little out of it, but Dean found himself laughing. “Agreeing that you might be better than Azazel isn’t saying much.”

He shrugged. “I’ll take what I can get.”

Meg sighed irritably. “You’re good to go, Dean-o. But I’m sure I’ll be seeing you again soon enough.”

“Yeah, probably,” Dean sighed as he sat up gingerly. If he even survived the next go-round.

Crowley reached out a hand to help him. “You okay?”

“Yeah.” He pulled away from his hand as he got to his feet. “Just peachy. Let’s go.” Even though he’d just woken up, he was exhausted, and he was ready to get back to his cell and sleep. Besides, both Meg and Crowley set him on edge, so the sooner he could get away from the both of them, the better.

Crowley led him to the door without comment, and they began making their way back to his cell.

“The answer’s still no,” Dean said after a few seconds, deciding that he might as well get it out there.

Crowley looked at him incredulously. “Do you have a death wish?”

He shrugged. “Not really. Probably would be better than feeling like this, though,” he admitted.

“There is a third option,” he pointed out.

Yeah, and after this last encounter with Alastair, Dean couldn’t help but wonder if Crowley’s option might actually be the best. He was still determined not to give in, though. On principle. “Not from where I’m standing.”

Crowley shook his head. “Out of all of the stubborn people I have met in here, Dean – you are something else.”

“Thank you.”

He looked at him out of the corner of his eyes, appraising him for a few seconds in silence. “What will it take?” he finally asked.

Dean looked at him in surprise. “What?”

“What will it take to get you to agree to my deal?” he asked slowly, enunciating each word.

He shook his head. “There’s nothing you can offer me, Crowley.”

“Oh, everyone has something that will push them over the edge. What is it for you? I have connections like you wouldn’t believe, and I can make a good number of things happen for you. All you have to do is say the word.”

Damn, Crowley was really trying to win him over, and that made Dean even less inclined to agree to his deal. Whatever it was Crowley wanted him for, he didn’t want to be a part of it. “No,” he said firmly.

“Fine,” he sighed. “I’ll have to find it on my own.”

“Well, better find it before Alastair kills me. I won’t be much good to you dead.”

“Oh, don’t worry. I will.” He sounded confident enough in that fact that Dean felt a little nervous. He didn’t let it show on his face, though; he just remained silent as Crowley deposited him back in his cell.

The next few days passed without incident. Either Dean was getting good at avoiding Alastair, or the guard had just decided to give him a reprieve. Maybe he was hoping to lure him into a false sense of security.

“I still say you should take Crowley up on his offer,” Benny said at breakfast one day as Dean scanned the room for any sign of Alastair.

“No way,” Dean muttered. He saw Gabriel, Uriel, Brady, Zachariah, and Raul, but thankfully, no Alastair. He breathed a sigh of relief.

“Dean, I saw you the other day – he really did a number on you. And you’re still lookin’ over your shoulder for him constantly. You shouldn’t have to live like that.”

“I don’t care,” he sighed as he turned back to face him. “I can’t give into Crowley. I just can’t.”

“This won’t end well for you.”

“I know.” Movement out of the corner of his eye caught his attention, and he turned as Crowley entered the room, his expression extremely tense. “Speak of the devil,” he muttered as the guard made a beeline for Gabriel, pulling him aside urgently. Dean frowned. “Wonder what’s going on?”

Benny glanced over at them. “No tellin’.” Unconcerned, he turned back to his food, but Dean couldn’t help but notice that as Crowley spoke, Gabriel’s expression was turning more anxious. What the hell could be going on that would make the both of them look like that?

“Something’s wrong.”

Benny’s gaze flickered over to the guards again, then back to Dean. “It could be personal,” he suggested.

“Yeah… maybe….” Crowley and Gabriel were friends, after all, but Dean had a gut feeling that this was something more than that.

Gabriel brought his hand up to Crowley’s shoulder as though ushering him to move, and sure enough, Crowley spun around and left the room as quickly as he had come. Gabriel pulled out his phone, punching in something frantically before bringing it to his ear. The conversation only lasted a minute, then he turned to scan the cafeteria until his eyes locked with Dean’s, and he began moving in his direction. Oh, this really couldn’t be good.

“Dean, I need you to come with me,” Gabriel said as he drew level with their table, his voice low and tense.

Benny raised his eyebrows slightly, while Dean looked up at the guard apprehensively. “What’s- ?”

_“Now.”_

Dean’s eyebrows shot up as he got to his feet, his brain working furiously to try to come up with what Crowley could have possibly said to make the normally relaxed guard so on edge. As soon as they were out of the cafeteria, Gabriel grabbed hold of his arm and pulled him down the hall.

“Gabe, what the hell is going on?” Dean demanded.

“Azazel’s escaped,” he muttered through gritted teeth.

Whatever possible conclusions had been developing in Dean’s mind, it hadn’t been that. He suddenly felt like he was going to be sick. _“How?”_

“I don’t know,” Gabriel said bitterly, not slowing his pace. “But I’d say Lucifer had something to do with it. And probably Alastair, too.”

Dean could hear the faint footsteps of a guard approaching from around the corner. A second later, Gabriel pulled him into a closet, shutting the door behind them and motioning for Dean to stay quiet. So, whatever Gabriel was planning to do wasn’t in the rule book, then. It at least gave Dean a little peace of mind to know that the guard had _something_ up his sleeve.

As soon as the footsteps had faded away, they were on the move again. Dean opened his mouth to ask what they were doing, but Gabriel was already speaking again. “Crowley’s calling up some connections – trying to see if any of them can help – but he’s not confident in any of them getting to him in time. Neither of us can leave in the middle of our shift – especially if we’re right about Lucifer’s involvement. We think we have a pretty good idea of where he’s heading, though.”

Yeah, so did Dean. “My place.”

He nodded gravely as he pulled him into the laundry room. “I’ve called a cab – it’s waiting right outside with directions to your place and instructions to gun it as soon as you’re inside.”

Dean blinked as Gabriel released his arm and walked over to grab a chair. “Wait, what?”

“I’ll call Cas, but he’s not as close,” he explained as he climbed up on the chair to push the cover off a vent in the ceiling. “It could take him several more minutes to get to your house, and with the time Azazel escaped, we’re cutting it close as is.”

“So, you’re breaking me out?” Sure, Gabriel wasn’t a stickler for the rules, but even so….

He jumped back down and turned to face him. “You got a better idea? Just don’t tell anyone it was me that helped you – that _includes_ Crowley – we’re close, but not that close.”

Well, if he wanted to take the risk, that was his choice. Dean wasn’t going to waste any more time arguing about it – he needed to get to his family. “Thank you,” he said fervently as he climbed onto the chair and hoisted himself up into the vent.

“Just continue straight for a few feet,” Gabriel instructed as he grabbed onto his legs to help him up. “Then you’ll see a grate above you. You’ll come out on the roof, and there’ll be a fire escape to your left. The cab should be waiting right beneath it.”

“Got it,” Dean grunted as he pulled himself fully into the vent. He set off in an army crawl as he heard the sound of the vent being closed up behind him. It only took him a minute to reach the grate that led to the roof. He popped it off easily, climbed onto the roof, then sprinted to the fire escape. The adrenaline pumping through him told him that it would be much faster to just jump off the roof, but he wouldn’t do his dad and Sam any good if he got himself killed before he could get to them. So, he took the slower, safer route, and sure enough, a cab was waiting at the bottom. He practically flung himself into the backseat, and immediately, the cab took off.

“Uh, I know what this looks like…” Dean started awkwardly after a couple of seconds.

“I don’t ask questions,” the driver assured. “Your friend paid me enough money not to.”

“Right,” he sighed as he leaned back against the seat. Well, there was that, at least. Now he just hoped he’d get there in time.


	8. Azazel

When the cab pulled up outside the house, everything looked calm and serene. Dean wanted to take that as a sign, that it meant he’d gotten there in time – that he could warn his dad that Azazel was on his way, and there would be plenty of time for them to clear out – but he knew better than to let his guard down.

He thanked the cab driver as he shot out of the car and sprinted for the door. It was surreal stepping inside the house after so long away. It was all exactly as he remembered it – not that he’d expected his dad would redecorate, but it still felt odd seeing the tattered, old furniture, the pictures of himself and Sam on the fireplace…. He suddenly realized it was because, even though he hadn’t been in prison for that long yet, it was already changing him. And now he was stepping back into his old life, where everything was just as he had left it, and he felt out of place as the new person he was becoming.

He shook the feeling off. He just needed to worry about finding his dad and Sam. They weren’t in the living room, so…

“Now, John,” a voice that Dean didn’t recognize floated down from upstairs. “I know you had help. And I am just dying to know who it was.”

Crap. A thrill of fear shot through Dean, and then he sprang into action. He moved swiftly and quietly to the gun cabinet, all the while straining to hear what was going on upstairs.

“See, I know your oldest is in prison, and if I know Alastair, he won’t be lasting too long. And I have unfinished business with this one.”

Dean’s jaw clenched as he grabbed the hunting rifle and loaded it. His dad had taken him hunting a few times as a kid, and while it had never been his favorite thing in the world, he was glad for the fact that it meant there were firearms in the house and he knew how to use them.

“Leave them out of this,” John begged – Dean had never heard his dad beg before, he had always figured he was too strong of a person to beg. “Please. This is between you and me.”

“Well, that’s really your choice, Johnny-boy,” Azazel taunted as Dean started up the stairs. “Either tell me who helped you – and then I’ll kill you, of course – or I’ll kill Sammy here, and let you live with that.”

“Dad, don’t-” Sam started.

“Crowley,” John interrupted, and Dean barely stopped himself from stopping in shock at the sound of the name. “His name was Crowley.”

Azazel scoffed as Dean reached the upstairs landing and drew level with Sam’s bedroom. “Figures.”

The gunshot went off just as Dean was lining up his shot. Dread flooded through him, but he pushed it down as he tightened his index finger and pulled the trigger. The bullet struck home in Azazel’s head, and he fell to the ground, dead.

“Dad!” he heard Sam scream as if from far away as he slowly lowered the gun to the ground. He didn’t want to look to where his brother had just fallen to his knees. He didn’t want to see… “Dean…” Sam hadn’t said his name like that since he was a little kid and he’d had another bad Mother’s Day experience at school. It was the tone he used whenever he was hurting, and Dean was always the only one who could make it better.

He was moving over to Sam without even thinking about it, reaching down to grip his little brother’s shoulder tightly as his gaze landed on his father. He had hoped for a split second that Azazel would be like Alastair – that he would try to draw out John’s suffering before ending his life, but the bullet had gone right through his chest, killing him instantly. Dean stood there in mute horror, unable to tear his eyes away, his grip on Sam the only thing that was grounding him.

After a few seconds, his brain kicked into action. He needed to get Sam out of there – staring at their father’s corpse couldn’t be good for him. “C’mon,” he muttered, moving his hand to grip under Sam’s arm, tugging him to his feet.

It really spoke volumes of the state Sam was in that he complied wordlessly and followed Dean down to the kitchen. He sat down at the table, and Dean poured him a glass of water, then grabbed himself a beer from the fridge and sat down across from him.

They drank in silence for a couple minutes before Sam spoke up, his voice shaky. “How’re you here?”

“I had help,” Dean muttered, his voice dry and cracking with suppressed emotion. “Can’t say too much.”

He nodded mutely. Another minute of silence, save for the sloshing of liquid and the clicking of glass against the table. “Who was he?”

Dean hesitated. He may not have wanted Sam to know about Azazel, but he didn’t really have a choice, anymore. And after what he had seen… he deserved to understand what had just happened. “Azazel.” He took another drink, choosing his next words carefully. “He’s who set the fire.”

Sam’s eyes went wide, and his glass fell the last couple inches to the table, tipping over and spilling its contents. Neither of them paid it much mind. “Dad said the fire was an accident.”

“Yeah. I know,” he sighed. “Azazel has powerful friends – I’m pretty sure that he was worried that us knowing too much would put us in danger.”

His gaze sharpened. “Powerful friends in the prison, you mean. That’s what’s been going on – why you’ve been targeted so much.”

Dean nodded. “Azazel was a guard there. I guess Mom did some volunteer work, caught his attention, and when she turned him down…” He trailed off, unwilling to tell Sam that he had been the real target in that fire.  “Anyway, Dad got hold of some evidence, got him put away, and now the rest of the guards are taking it out on me.”

Sam shook his head in disgust. “Why doesn’t the warden-”

“Cause he ain’t any better than the rest of the guards, and Azazel was the teacher’s pet.”

“Of course he was,” he muttered bitterly. He sighed as he got to his feet and grabbed a paper towel to wipe up the water. “So, any idea who the Crowley was that Dad got his information from?” he asked after a minute, clearly trying to keep the conversation going to avoid thinking about what had occurred. Dean didn’t blame him. He would even be grateful for it if it weren’t for the fact that this wasn’t something that he wanted to discuss with him.

“One of the guards at the prison,” he answered, staring at the bottle on the table in front of him with narrowed eyes. “The bastard doesn’t do anything for free, though; so, Dad must’ve done something in exchange.” He wondered why Crowley had never brought it up while trying to strike a deal with him – maybe he had been worried that Dean would sell him out to Alastair. And honestly, he didn’t know if he would have or not. On the one hand, he would have never wanted to give Alastair anything that he wanted. But on the other, he didn’t want to do Crowley any favors, either. It would just come down to who he would want to spite more, and the answer to that question changed depending on which one he had spoken to most recently.

“And he said as much, didn’t he?” Sam pointed out as he reclaimed his seat. “When we first came to visit you, Dad said that he wasn’t proud of how he got the information.”

“Yeah,” Dean sighed. “Guess he did.” He supposed Crowley had had a point when he said that everyone had something that would push them over the edge. He had just never figured that that was true of his dad – the man had always been so unyielding, never letting anyone sway him one way or the other. Still, if his breaking point was finding justice for Mary, Dean could never blame him for that. The only reason he wished John hadn’t done whatever he did was because maybe then he would still be alive….

He looked down at his lap, determined not to cry. At least not in front of his brother. He needed to be strong for him. So, he gritted his teeth and held back the tears that threatened to overcome him.

“Dean…” Sam asked hesitantly after another few minutes of silence.

“Hm?”

“…What did Azazel mean when he said he had unfinished business with me?”

Dean squeezed his eyes shut tight. No, he couldn’t answer that. How was he supposed to tell his little brother that Azazel had tried to kill him when he was just a baby? That the fire that had killed their mom had been intended for him? Sam would never see things the same way again. He would start blaming himself for her death, and Dean couldn’t let that happen. “Dunno,” he muttered instead.

“You’re lying,” Sam accused, and Dean looked up to see him glaring at him through narrowed eyes.

“Look, it doesn’t matter, okay?” Dean tried desperately. “Azazel’s dead.”

“It matters to me. Dean, how would you feel hearing that and not knowing?”

“I’d hate it,” he admitted. “But that doesn’t mean I’d be right to want answers. Sometimes ignorance is bliss.”

“Well then, maybe Crowley knows. I’ll just track him down, and-”

 _“Fine!”_ Dean interrupted as panic shot through him at the very idea of his brother striking up a deal with Crowley. He shook his head, running a hand over his face. “Azazel told Mom that if she didn’t leave Dad for him, he’d…” He took a deep breath, his gaze shifting to the wall to his right. “He’d kill you.”

Sam was silent for a few seconds as that sank in. “The fire was started in my nursery,” he said hollowly.

He nodded. “Guess Mom was staying in there… just in case.” When he finally found the courage to look back at his brother, there were tears sparkling in his eyes. “Look, Sam…”

“I should’ve been the one to die that night,” he muttered, his voice barely more than a whisper.

“No,” Dean said firmly.

“Maybe if he’d actually killed me, he wouldn’t have come back for Dad! Mom would still be alive, you wouldn’t be in prison…”

“Hey!” He reached out, gripping his brother’s shoulder across the table. “There’s no telling what would’ve happened, and there’s no use speculating on it. They’re not dead because of you. The only person that can be blamed is Azazel. And you know what? If Mom and Dad were here, they’d tell you the same thing.”

“But they’re not here, are they?” Sam challenged, pulling out of his grip, a couple of tears escaping down his cheeks. “Dad’s dead upstairs because Azazel said it was me or him, and the only reason he was in that position was because I didn’t die when I was supposed to.”

“You weren’t _supposed to_ die, Sammy! You can’t beat yourself up over this. What’s done is done, and we just have to deal with it.”

He shook his head. “How can you say that?”

“Because Dad is dead, and there’s nothing we can do about it! And you know, I wish more than anything that I had gotten here just a _couple seconds_ sooner. I keep replaying everything in my head, thinking of every instant where I wasted precious time, where if I’d just _hurried,_ Dad would still be alive right now. But it doesn’t change anything. I can replay it all over and over and _over_ again, and he’ll still be dead….” Dean took a shuddering breath, wiping a stray tear from his cheek.

All the fight drained from Sam’s expression. “Dean, I’m sorry…. You know it’s not your fault.”

But it was. He’d missed saving his dad by _one second._ Why hadn’t he gotten up there faster? “It’s not yours, either,” was all he said aloud.

Sam sighed. He opened his mouth to reply, but then his gaze snapped to the window as the unmistakable sound of a car pulling into the driveway reached their ears. They looked at each other, their eyes cautious.

“You should stay here,” Sam said softly as he got to his feet. “I’ll get it.”

Dean was about to protest, but then there was a knock at the door, and Sam quickly left the room. There were a number of possible options as to who could be at the door, and Dean hoped to God that whoever it was, it wasn’t Alastair. He suddenly found himself wishing that he hadn’t left the gun upstairs. He stood and moved quickly over to the counter, grabbing a knife from the drawer as he heard Sam open the door.


	9. Tipping Point

“Who’re you?” Dean heard Sam ask from the living room, his voice defensive and on edge.

“My name is Castiel,” a second voice answered, and Dean breathed a sigh of relief as he let the knife he was holding drop back into the drawer. He had thought it would be pointless to hope for the best-case scenario, but it looked like he was catching a break for one. Well, he’d more than earned it.

“You are Sam Winchester?” Sam must have nodded because Castiel continued, “I am a guard at your brother’s prison.”

“Great,” Sam replied coldly. “Get out.”

Dean hurried from the kitchen, walking into the living room as Castiel was attempting to prevent the door from being shut in his face. “Sam! Sam, wait. It’s okay. He’s a friend.”

Sam glanced from Castiel to Dean, then back again, his expression incredulous. Meanwhile, Castiel blinked at Dean in surprise. “Dean? How are you here?”

“Um…” Dean looked around uncomfortably, unsure if he should tell Castiel that his brother had sprung him. Gabriel had told him not to tell anyone, but it wasn’t like Castiel would turn him in. Still, it was probably best to keep it to himself for now, and if Gabriel wanted to tell him, he could.

Castiel sighed. “Gabriel.” Well, so much for that.

“No,” he immediately refuted. “I got out on my own.”

The look Castiel fixed him with was one of pure disbelief. “I appreciate you trying to cover for him, but I know my brother.” He shook his head. “And he says that the things _I_ do are risky.”

“Well, they are.”

He shot Dean a glare before turning back to Sam. “May I come in? I assure you, I only want to help.”

Sam finally seemed to relax, and he nodded and stepped back, allowing Castiel to walk into the house. It was odd seeing him in something other than his uniform, and in Dean’s personal opinion, it was a little warm for a trench coat. Concerned eyes flickered around the room before they landed on the elder brother. “Dean, what happened?”

Dean looked down as sorrow washed over his expression. “I was too late,” he muttered to the floor. “Azazel, he… he killed our dad.”

Castiel’s expression crumpled. “I am so sorry, both of you.” He looked from Dean to Sam, who was avoiding looking at either of them.

“Yeah, me too,” he sighed, then hesitated. Word getting out that he had killed Azazel was _not_ what he needed right now, but he knew that he should tell Castiel. “Azazel’s dead, too. I-”

“I killed him,” Sam hurried to interrupt.

Dean’s eyes grew wide as his gaze snapped to his brother. “Sam, you can’t-”

“It was self-defense,” he continued as though he hadn’t heard him. “He had just killed my dad right in front of me, and he was going to kill me next.”

“No, Cas, Sam didn’t kill him, I did,” Dean said quickly.

“Dean!” Sam rebuked desperately. “You’re already in prison for one murder, you can’t take the fall for this.”

“That doesn’t mean-” he started to protest, but Castiel cut him off.

“Sam’s right, Dean,” he said softly.

He looked at him in disbelief. “Cas, I _know_ you aren’t suggesting my little brother taking the fall for murder, when we all know I’m the one who did it.”

“I’m not,” Castiel assured. “I will take the fall for it.”

Both Sam and Dean’s eyes were as wide as saucers. “You can’t do that!” Dean objected.

“Yes, I can,” he argued calmly. “Out of the three of us, I am the most likely to get away with it. I came to check on your family, saw Azazel kill your father, and when he turned the gun on Sam, I reacted the way any guard should. It would certainly not be the first time a guard has killed a prisoner – escaped or not,” he added bitterly.

He did make a point, but… “You’ll lose your job.”

“Not necessarily. Lucifer will certainly want to fire me all the more, but protecting civilians is not breaking any rules.”

“No,” a familiar voice spoke from the open doorway. “But lying about it and aiding an escaped prisoner are.”

Ice settled in Deans chest as he turned to see Crowley leaning casually in the doorway, a broad smirk on his face.

Castiel spun around, his eyes narrowing. “You’re supposed to be at work.”

“Oh, did you memorize the days I work?” Crowley mocked as he walked into the house. “That’s sweet, Cassie. But actually, my shift ended fifteen minutes ago. Lucky for you.”

“How is that lucky for me?” Castiel demanded coldly.

“Because you can’t hope to get out of this situation without me,” he said as though it were obvious.

“It sounds more like you’re threatening than helping,” Sam spoke up, his arms crossed over his chest as he eyed Crowley apprehensively.

Crowley turned to him with raised eyebrows. “Well, I see that brazenness is a family trait.”

He fixed him with a steady glare. “It sure is. So, why don’t you cut to the chase?”

He grinned, his eyes flickering over to Dean, who was watching him cautiously. He had a pretty good idea as to where this was heading, and he didn’t like it. “You really should learn some manners,” he said, returning his gaze to Sam. “Considering I could have all three of you arrested – twice, in Dean’s case.”

“I knew Gabriel was wrong about you,” Castiel muttered. “You’re just as loyal to Lucifer as the rest of them.”

Crowley turned to him with a glare. “I am _not,”_ he growled. “And one would think, with the war you are waging against your brother, you would want as many allies as you can get.”

“I would never consider someone like _you_ an ally.”

“Okay, you two,” Dean sighed. “Stop comparing dicks. Crowley, get to the point.” He saw the surprise flicker across Sam’s face at the name, and he looked to Dean with a questioning look. Dean shook his head subtly enough so that Sam was the only one that noticed – it was probably for the best that Crowley didn’t know what they knew, at least for the time being.

Crowley grinned, clearly tasting victory. “Castiel’s story has merit,” he admitted. “But there’s one little problem – you. If it’s discovered that you escaped, Lucifer will spare no resources investigating, and he is bound to find who helped.” He nodded to Castiel cordially before turning back to Dean. “And while you undoubtedly don’t care about the consequences to yourself, I am sure you are noble enough to care what happens to your little friend. I think we both know that Castiel doesn’t have the resources or leverage to properly cover up your escape, but I do. So, what do you say, Dean?”

“That sounds an awful lot like blackmail,” Sam interjected before he could respond.

“I’m just stating facts,” he said smoothly. "And I’m not asking you, am I?” He turned back to Dean. “I’m asking you. What’s it gonna be?”

Dean took a deep breath as he met Crowley’s gaze levelly. He could read between the lines, he knew what he was really asking. Sam was right, it was blackmail, but Crowley couldn’t exactly come out and say that in front of Castiel. And Dean didn’t even have to think about it. He knew what his answer was. Everyone had a tipping point. There was no way that he could let this whole mess come back to hurt Castiel or Gabriel. The way he saw it, there was no longer a choice. “Yeah,” he muttered. “We could use your help.” He didn’t even have the faintest idea of what he was agreeing to, what Crowley would require from him in exchange. But he had probably forfeited the right to know in advance when he’d turned him down the first several times.

Crowley’s eyes were dancing with glee, but he otherwise kept his expression composed. “That’s what I thought.”

“Dean, are you sure?” Sam looked over at him worriedly, while Castiel merely glared at Crowley.

“Yeah,” Dean nodded without looking away from Crowley. “We need his help – he’s the only way we’re all going to get out of this. If he is intending to screw us over, well… we’re already screwed, anyway.”

“Exactly,” Crowley agreed, clapping his hands together. “So, Cassie, wipe Dean’s prints off the murder weapon, get yours on it, then call the police. Moose, you just be a good boy and stick to Castiel’s story. Squirrel, you’re coming with me.”

Dean rolled his eyes at the nicknames as he walked over to pull his brother into a hug. “You’re gonna be okay, Sammy,” he muttered. “Call Uncle Bobby – I’m sure you can stay with him until you’re off to Stanford.”

Sam scoffed, shaking his head slightly. “I don’t know how I can even think about Stanford right now.”

“Hey,” he said firmly. “You can’t do that. Your life is still going, and you can’t give up on your dreams just because everything else is going to shit.”

“Yeah… okay,” he muttered unconvincingly. He changed the subject before Dean could press the point further, though. “You know I’m eighteen now, though, right? I _can_ stay on my own.”

Dean sighed. “Given what just happened… I’d feel better if you stayed with Bobby.”

Sam looked like he was about to argue, but there must have been something in the look on Dean’s face because he relented. “All right,” he sighed.

“Good.” He gave his shoulder a reassuring squeeze. “See ya, Sammy.” He turned and walked over to where Crowley was waiting by the door, clapping Castiel on the shoulder along the way. “Thanks for everything, Cas. I owe you, like, twenty.”

Castiel inclined his head. “I am happy to help, Dean.” His gaze flickered to Crowley, then back again. “Be careful.”

He nodded. “I will.” He turned to Crowley. “Ready to go?”

“More than,” Crowley answered smugly as he turned and walked outside, Dean following behind him. He opened up the passenger’s door of his Bentley for Dean, then walked around to get in the driver’s side.

“I bet you’re real happy about all of this,” Dean muttered after Crowley pulled out onto the road.

“I can enjoy the outcome without liking what caused it,” he corrected. “I am sorry about your father.”

“Yeah, I doubt that.” He turned away from him, looking out the side window.

“I am,” he insisted. “I had hoped to get to your house in enough time to prevent this.”

“But you didn’t, so you settled for blackmailing me instead,” Dean threw back in his face.

“I’m a businessman, Dean. I saw an opportunity, and I had to take advantage of it.”

“Whatever,” he sighed. “What is it you want from me, anyway?”

“Just your services,” Crowley said as though that should set his mind at ease.

He raised an eyebrow. “Sexual services?” He hadn’t pegged Crowley for the type to go to such lengths just to get laid, and if that was the case… well, it wasn’t as though Dean wasn’t attracted to him, but the entire situation was a bit of a turn off.

He chuckled. “That’s entirely up to you. What I really require, though, is information.”

Dean’s eyebrows furrowed in confusion. “Information?”

“Oh, yes. Information is quite possibly the most valuable thing in the world, and most prisoners are sitting on more treasure than they know.”

“So, what do you expect me to do?” he asked, not quite following.

“It’s quite simple. You’re attractive, charming – you have a way with people. A couple well-chosen words from you and anyone will be spilling their secrets. And that’s precisely what I want. Information on those outside the prison is the most valuable, but if there’s a prisoner who might be _particularly_ useful, I wouldn’t mind some dirt on him, too.”

“So that you can blackmail more people into doing your dirty work, you mean?” Dean accused.

Crowley merely smiled. “Do you think you can manage that, Dean? Or should I tell Lucifer what Castiel is up to?”

“Oh, I can manage,” he muttered bitterly. “So long as you hold up your end of the bargain. I dig up information for you, you keep your mouth shut about what really happened today and protect me from the guards.”

He raised his eyebrows as though surprised. “Oh no, Dean. You turned down the protection. This is no longer a negotiation, it’s blackmail.”

Dean glared at him through narrowed eyes. “Really?” he pressed. “’Cause it seems to me that it’ll be a bit hard for me to dig up information for you if I’m too busy being beaten to death.”

He had expected Crowley to be angry at his insolence, but instead the guard smiled, seemingly almost impressed. “I knew there was something special about you,” he murmured as he slowed to a stop at a stop sign and looked over at him. “Okay, you’ve got yourself a deal. Care to seal it with a kiss?”

He rolled his eyes and turned away, pretending that he wasn’t a tiny bit tempted. “No thanks.”

“Your loss.” He shrugged as he turned forward again and accelerated.

Dean sighed as he watched the houses and his old school flash by outside the window. So much for keeping the last of his freedom. Now he was stuck being Crowley’s bitch unless he could find some way to get out of it.


	10. First Day on the Job

“Damn,” Benny breathed.

“Yeah,” Dean sighed, laying back on his bed. “Tell me about it.” He could feel Benny watching him, but he carefully schooled his expression as he stared at the bottom of the bunk above him.

“You okay?” Benny finally asked.

“I’m fine,” he muttered, his voice emotionless.

He could hear footsteps approaching him. “Nah, you’re not. And you shouldn’t be – not after what you just saw.”

“Yeah, well, I’m dealing.”

“Now, I’m no expert. But I’m pretty sure suppressin’ your emotions isn’t dealing.”

Dean looked over at him. “So, what am I supposed to do? It’s not like I can afford to be emotional in this place. I’ll be eaten alive.”

“It’s just you and me right now,” he pointed out. “No one else is gonna see a thing.”

He shook his head, turning his gaze upwards again. “I don’t suppose you have any useful information on the pirates you used to run with?” he changed the subject.

Benny sighed, and for a second Dean thought he was going to keep pressing his point, but he seemed to realize that he was never going to get anywhere. “If I come up with anything that might interest Crowley, I’ll let you know,” he said resignedly.

“’Preciate it.”

They were silent for a few seconds. “It’s not that bad a deal, really,” Benny commented. “I mean, what Crowley pulled off, coverin’ up your escape was no easy feat.”

“Oh, I don’t know,” Dean muttered bitterly. “Knocking me out and leaving me in some overlooked corner didn’t seem too difficult for him.”

“Better than the alternative.”

He shrugged.

“But gatherin’ information isn’t such a bad price to pay,” Benny continued.

“Yeah, information that he’s going to use to blackmail even more people,” Dean snapped as he turned his head to the side to glare at Benny.

“I didn’t say it was good,” he amended. “But it could be worse.”

He shook his head, swinging his legs over the side of the bed to sit up. “I’ve gotta find a way out of this.”

“How?”

“I don’t know.” He stared at a spot on the floor, his eyebrows furrowed as he thought. “But I’ll find something,” he said with determination.

“Outsmartin’ Crowley won’t be easy,” Benny warned.

Dean looked up at him, managing a small smirk. “It’s a good thing I’m not just a pretty face, then.”

Of course, he wasn’t going to figure out a way to get out of his deal overnight. He knew that. He’d have to play along for a bit, make Crowley think that he would uphold his side of the bargain, no questions asked. Besides, working for Crowley was as good of a distraction as anything from his life right now.

“This seat taken?”

The man looked up at him, his expression curious. “You’re Dean Winchester, right? Number one on the guards’ most hated list?”

“Yep, that’s me alright,” Dean said with a grin.

He nodded. “Have a seat. I’m Gordon Walker,” he added as Dean sat down.

His first impression of Gordon was that he was an alright guy. He identified with him – they had a lot of common interests, and they had both ended up in prison because they had killed for their sibling. The difference was, for Gordon it was out of revenge. A gang had gotten hold of his little sister – he didn’t go into detail, and Dean figured he didn’t want to know. He felt bad for the guy. He couldn’t imagine if anything happened to Sam… that just wasn’t something he could bear thinking about.

“And you killed all of them?” Dean asked.

“Everyone I could find,” Gordon said proudly. “I think a couple might’ve slipped by. I was tracking them when the police caught up with me.”

“Bet that’s hard. Knowing they’re still out there.”

He shrugged. “It’s only temporary.”

Dean tilted his head curiously. “What do you mean?”

“I have friends,” was all Gordon said.

He frowned. “And they’re gonna take them out?”

“Sorry, Dean,” he shook his head. “I like you and all, but some information is best kept private.”

Bingo. “Hey, I get it,” Dean sighed, leaning back in his chair. “I only ask cause… well, Dick Roman tried to kill my brother, Azazel killed my father – neither of them operated alone, and I _hate_ knowing that they have allies still kicking out there. I know how you feel.”

Gordon nodded thoughtfully before he leaned in, resting his elbows on the table. “One of my friends works at the NSA – he can track people. Another, well… let’s just say he’s very skilled in certain areas. I might be able to swing a favor for you.”

His eyes widened as though shocked and touched by the suggestion. “That’d be awesome.”

He nodded as he leaned back. “I’ll see what I can do.”

Later that day, Dean was unsurprised when Crowley came to see him while he was working.

“How goes your first day on the job?” he asked as he strolled up to where Dean was folding clothes.

“I got some information from Gordon Walker,” he said, his voice monotone.

Crowley raised his eyebrows. “Already? Color me impressed.”

Dean gave him an odd look. He had already gotten him to work for him, so why was he trying to butter him up? He highly doubted that Crowley was _actually_ impressed. Why else would he have come by if not because he expected him to have some information? “He has a friend in the NSA using government resources to do him personal favors,” he said shortly. “He didn’t give me a name, but I figure you can find that out easily enough.”

Crowley’s eyes lit up at the information, a smile curling up his lips. “Indeed, I can. And that will go a long ways. Now, from the sound of it, you also got some juicy details on Mr. Walker. Do spill.”

“I don’t know what you’re talking about,” he muttered as he folded a jumpsuit.

“Oh, I doubt that. Don’t hold back on me now.”

Dean rounded on him with a glare. “Isn’t what I told you enough? Come on, Gordon’s a good guy, he doesn’t need this.”

Crowley’s eyebrows sprang up, his expression amused. “A good guy? I don’t think you know him as well as you think.”

He frowned slightly. “What are you talking about?”

“What did he tell you about how he ended up in prison?” he asked curiously.

“Some gang killed his sister and he got revenge,” Dean said with a shrug. “Can’t say I blame him.”

“Except the gang _didn’t_ kill his sister.”

His eyebrows furrowed in confusion. “What?”

“She _joined_ the gang. In Gordon’s mind, they had corrupted his innocent little sister, and he wouldn’t stand for that. So, he bombed their headquarters, killing the lot of them… _including_ his sister.”

Dean blinked in shock as Crowley’s words sank in. “Holy shit,” he muttered. “That’s messed up.”

“Mm-hm,” Crowley hummed with satisfaction. “So. Feeling more inclined to share, now?”

He sighed, looking away. “He’s having his friend track the surviving members of the gang. He said he has another friend who’s very skilled.”

“So, he’s arranging for them to be killed?”

Dean shook his head. “That’s what I thought at first, but… it doesn’t add up. His friend has their locations. Why wait?” He debated for a second over whether or not he should continue before deciding that Gordon needed to be kept in check, even if it was by Crowley. He sighed. “I think his other friend is going to break him out. Then he can kill the surviving gang members himself.”

“I see…” Crowley mused thoughtfully. “Well, the world certainly does not need the likes of him on the loose. If you’re right, I’ll put a stop to his little scheme.”

He looked at him in surprise. “You’re not just going to blackmail him?”

He shook his head. “For one, I’m not sure how much good he would do me. But mostly, I don’t like him, and I don’t like the idea of him getting out.”

After what Dean had just learned about Gordon, he couldn’t say he felt any differently. He was still surprised that someone as slimy as Crowley felt that way, though.

Crowley arched an eyebrow at him. “Do you disagree?”

“Um…” He scrambled for a moment, surprised that Crowley cared enough to ask. “No. I think he deserves to be locked up.”

“Good. That’s settled, then,” he said decidedly.

Dean stared at him in confusion. That made it sound as though his opinion actually carried some weight, but… it didn’t, did it?

“You did well today, Dean,” Crowley continued. “You’re a natural. If anything else comes up, let me know.”

He nodded numbly as he watched Crowley turn and walk from the room. He really wasn’t sure how he felt about being called a natural at doing Crowley’s dirty work. On the one hand, this wasn’t something that he _wanted_ to be good at, but on the other… well, it felt good to receive a little praise. He sighed as he got back to work, feeling much more confused about this whole situation with Crowley than he had when he first made the deal.


	11. Problem Solved

Dean didn’t know where Crowley was – if his promise had been empty, or if this was just an honest mistake. Hell, maybe the guy had just bitten off more than he could chew when he had promised to keep Dean safe from Alastair. There could be any number of explanations, really.

All Dean knew what that when Alastair had initially cornered him, he had been confident that Crowley would intervene at any minute. As time wore on, though; he cursed himself for being so foolish. Looking on the bright side, he didn’t think he’d have to find a way to get out of his deal, anymore. But that was only because it was pretty clear that whatever had been holding Alastair back before had died with Azazel, and he had no intention of stopping until Dean was dead.

He wasn’t entirely sure why he was struggling so hard to remain conscious, despite the pain. It would be easier to let this all end. But whenever he started to slip, his brother’s face swam before his eyes. Sam had already lost so much, and Dean could see the toll it had taken on him. How would he react to losing his brother, too? He had to try to hold on – for Sam, if for nothing else. He had to…

But there was only so long he could hold onto consciousness through sheer willpower, and eventually the darkness overtook him.

*

Dean’s first clue that he wasn’t dead was the sound of Meg’s irritable voice. If he was in Heaven, she certainly wouldn’t be there, and if he was in Hell, he was sure he’d be dealing with much worse than her. So, he must still be in Purgatory.

He listened, not having the strength or willpower to open his eyes just yet. “You don’t have to stand over me, you know,” she snapped. “I am perfectly capable of doing my job. So, why don’t you get back to yours?”

“I am doing my job,” Crowley replied calmly, his voice coming from Dean’s other side. “I’m guarding a prisoner.”

“And he’s in _my_ care. I’m not sure you realize it, but you are actually responsible for more prisoners than just Dean Winchester.”

There was the sound of movement as Crowley stepped closer. “Yes, but if I leave now, he’s in bad enough shape that no one will look to closely if you are to say there was nothing you could do to save him.”

“I don’t like your accusation,” she said coolly.

“I don’t like you. And I don’t trust you. And if Dean dies, I will take it out on you. And frankly, I find Alastair’s methods to be a little… unimaginative.” A chill went down Dean’s spine at the menace in Crowley’s voice. It wasn’t necessarily unpleasant, though; it felt good to have someone so protective over him, even if that person was Crowley.

“That sounds an awful lot like a threat, Crowley. I wonder what Lucifer would have to say about that if I told him.”

“Nothing,” Crowley said confidently. “He doesn’t give a damn about you, or any of us, for that matter. When has he ever cared when we fight amongst ourselves?”

“He cares about me,” she shot back haughtily.

“Whatever you say.” Dean could practically hear his mocking smile in his voice. “And if you want to run to him, be my guest. Go disturb the warden from his work to complain that a guard has threatened you, and you need him to come defend you.”

“I never said I couldn’t defend myself,” she snapped. “You don’t know what all Alastair taught me.”

“If all you learned you learned from him, I’m not afraid of you.”

She scoffed. “Why don’t you take a look at your favorite little pet and say that again?”

“He’s not my pet,” Crowley objected, his tone almost bored.

“No? Then why do you bend over backwards for him?”

He was silent. Dean couldn’t hear anything aside from his own heart thudding in his chest. But Crowley didn’t bend over backwards for him. Sure, he had certainly taken an interest in him, but that was only because he’d wanted to make a deal with him. And now he had, so it only made sense that Crowley was here making sure he was safe. It was only because he was working for him, not because of _him._

“You’ve taken an interest in prisoners before,” Meg continued. “But never like this. Why him? I mean, sure he’s nice to look at, but he’s not _that_ special.”

There was a pause. “I don’t know what you’re talking about,” Crowley denied smoothly. “I simply feel that it’s my duty to make sure he’s safe.”

She snorted. “Nobody who knows anything about you will believe that.”

“Then it’s a good thing I’ve never cared what anyone else believes.”

Dean faded back out of consciousness. When he came to again, there was a hand brushing his hair from his forehead. From the gentleness alone, he was pretty certain it wasn’t Meg, and when he opened his eyes, he saw Crowley looking down at him.

“Well now, look who’s finally awake,” he murmured as he pulled his hand back.

Dean glanced around the room, and upon seeing no sign of Meg, turned back to where Crowley. He had drawn up a chair and was sitting beside the table that Dean was laid out on. “Where’s Meg?”

“On her break, thank god. I wasn’t sure how much longer I could put up with her.”

“You could’ve left,” he pointed out.

“She would’ve killed you,” Crowley said severely.

Dean knew he was probably right – Meg had just lost her father, after all. He was sure she was itching for someone to take her anger out on. And he could relate. “I’m surprised I survived long enough to make it here, honestly,” he admitted. “I thought Alastair was going to kill me.”

“Oh, he was,” he assured him. “But _someone_ set up a hidden camera and sent the feed to the police. Alastair has been arrested.”

His eyes widened at the news. Alastair had been arrested. He couldn’t hurt him anymore. But even while relief coursed through him, there was also suspicion. “You let him get ahold of me,” he accused.

“It was a sure way to solve our problem.” There wasn’t even a hint of remorse in his expression.

Dean’s eyes narrowed. “We had a deal.”

Crowley immediately became defensive. “And I’ve held up my end! I promised to protect you, but there was no guarantee that I would be able to do so whilst Alastair was still a guard here. I realize this wasn’t exactly ideal, but it was the only way to keep you safe.”

He huffed, shaking his head slightly. As much as he hated to admit it, Crowley made a good point. The rest of the guards wouldn’t pose too much of a problem, but Alastair held more sway than Crowley did. Getting rid of him really did seem to be the only answer. But that didn’t mean Dean had to like it. “You son of a bitch,” he muttered, but there wasn’t much venom in his voice.

He arched an eyebrow. “I didn’t realize you’d met my mother.”

Dean’s eyebrows furrowed slightly, and then he burst out laughing. It hurt, but it also felt good to _genuinely_ laugh for once. Despite the pain, he didn’t want to stop – and honestly, he wasn’t hurting as much as he had figured he would be. “You know,” he said once his laughter had subsided. “For nearly being beaten to death, I don’t feel too bad.”

Crowley, who had been grinning ever since Dean had started laughing, inclined his head slightly. “That’s because I slipped you some anesthetic after Meg left the room.”

He blinked at him in surprise. “Why?” He hadn’t meant to ask it, the word had just come tumbling from his lips. Everything Crowley had done – setting up Alastair, staying by Dean’s side to protect him – could be explained away by their deal. It wasn’t as though Crowley actually _cared_ about him. Dean wasn’t stupid. And sure, it’d be nice to be cared for, but he didn’t need that from _Crowley._ But… what did giving him anesthetic have anything to do with their deal? 

Crowley frowned, obviously confused. “To relieve some of your pain, naturally. That _is_ the purpose of anesthetic, after all.”

“Yeah, I know that,” Dean snapped, his cheeks heating up slightly. “You just don’t strike me as the type of guy who does anything that doesn’t benefit you in some way.”

“You’re not wrong,” he admitted.

“So, how does giving me-?”

Crowley’s eyes flickered to the door briefly before he abruptly cut him off, his tone suddenly cool and commanding. “You know, Winchester, if you’re well enough to mouth off, then I’d say you’re well enough to go back to your cell. What do you say?”

“Wha-?” Dean started, but he understood as soon as Meg entered the room, her eyes darting between the two of them. “You can’t do that,” he snapped. “I’m still recovering.”

“I can do whatever I like. I suggest you keep that in mind.” He rose to his feet, his gaze moving to Meg. “He’s all yours. Just know that I’ll be stopping in frequently to ensure his wellbeing.”

She rolled her eyes. “I don’t work for you, Crowley.”

“I don’t care. I just expect Dean to be in one piece when he is returned to his cell, and I will do what I deem to be necessary to ensure that.” With that, he left the room.

True to his word, Crowley stopped in often throughout Dean’s stay in the infirmary. As did Gabriel and Castiel, and even Balthazar once – though he had only come on Castiel’s behalf. Meg was clearly frustrated with the lack of opportunity to do anything unsavory to Dean, but there wasn’t anything she could do about it.

All in all, Dean’s stay wasn’t too bad. And it gave him ample opportunity to think. Crowley had gotten two of the guards there arrested, and Dean was the only person with that knowledge. And Crowley didn’t even know that Dean knew about Azazel. If any of that got out…

He felt a little guilty just thinking the thought, all things considered. The information that Crowley had provided his father with was what had gotten his mom’s murderer arrested. And the evidence he had fed the police on Alastair had been for Dean’s own safety. And then he had been so diligent in making sure that Dean remained unharmed after the fact.

But the fact remained that Dean had to get out of his deal. And it wasn’t like he was _actually_ going to throw Crowley under the bus, he just had to make Crowley think he would if he didn’t let him out. But he knew he couldn’t even do that much if he didn’t have any solid evidence to use against him, and he hadn’t the slightest idea… or maybe he did…. It was a long shot, but he just might have a way out.


	12. Confusion

“Hey, Cas,” Dean said once he was finally released from the infirmary and Castiel was escorting him back to his cell. “I know, after everything you’ve done, I have no right to ask a favor of you, but-”

“What is it?” Castiel interrupted, his tone concerned and not in the least bit irritated that Dean had the audacity to ask yet another thing of him.

“If I give you Bobby’s address, can you go speak to Sam?” he asked hopefully. “Tell him that I need him to find Dad’s journal and then come see me?”

He frowned. “Why? Is everything okay?”

“Yeah, everything’s fine. I just… need to see something in it. Get some answers, you know?” The less Castiel knew about what he was doing, the better. It wasn’t that he didn’t trust him, but he had a pretty good idea of how the guard would react, and it wouldn’t be good for anyone involved.

Castiel didn’t say anything for a few seconds. “Do you think it is wise?” he finally asked. “To go prying into the same matters that got your father killed?”

Dean sighed. “It’s not like that. This is just something I have to do, okay? And if you don’t want to help, fine. But I will find some other way to get ahold of the journal.”

“No, I will help,” he said slowly. “I just hope you know what you are doing.”

 _Yeah, I hope so too,_ he thought to himself. This plan had the very strong possibility to blow up in his face. And then what would that mean for him?

“You are insane.” Benny shook his head after Dean explained to him what he was planning.

“It’ll work,” he protested, much more confidently than he felt.

“I’d say you have a fifteen percent chance of success. Fifty percent that it will end up backfiring on you, fifteen that it will go too far, and knowing you, you’ll find a way to feel bad about it, and ten that you won’t be able to find what you need in the first place.”

“Hey, at least I’m more likely to succeed than find nothing,” Dean pointed out.

Benny sighed. “How are you so sure that what you need will be in your dad’s journal, though?”

“You didn’t know my dad,” he said with a shrug. “The guy documented everything. And something as important as this… it’ll be in there.”

“Alright. So, let’s say it is, and you go through with this plan…. It’s a low blow, Dean.”

“You think I don’t know that?” Dean sighed. “But it’s what I have to do. And it’s not like I’m actually going to _do_ anything with it. I just have to make a point.”

“And what happens if things go too far?” he challenged. “Now, I don’t like Crowley, but you have a conscience. It’ll eat at you.”

“It won’t go too far,” he said firmly. He wouldn’t let it.

“And there’s your other problem.” Benny waved his hand as though motioning towards the words that had just left Dean’s lips. “If you’re not willing to _let_ it go too far, Crowley will pick up on that. And then all you’ll be doin’ is pissing him off.”

“I’m a good actor,” he protested. “And Crowley knows I hate him. It’s not too much of a stretch to think I’d follow through.”

“Do you?”

Dean blinked, confused. “Do I what?”

“Hate him?” he asked simply, his expression neutral.

“Of course I do!” he snapped defensively. “You know I do.”

“I know you _did,”_ he corrected. “But recently… I dunno, brother – you seem more confused than anything when you talk about him, anymore.”

“Just because the guy’s confusing me, it doesn’t mean I don’t hate him,” Dean objected.

Benny shrugged. “I s’pose.” He didn’t look convinced in the slightest, though; and honestly Dean couldn’t blame him. He wasn’t all that convinced himself, and it was pissing him off.

Crowley was awful – he blackmailed anyone he could get his hands on, and Dean was sure that it went deeper than that. The only thing that he cared about was himself, and if others got hurt, that was just fine, so long as he got what he wanted. But… there were some things he did that just didn’t add up. There was no telling what he could have gotten from Gordon, but instead he had been more concerned about a guy like him getting out of prison…. He had done everything he could to lesson Dean’s pain while he’d recovered from Alastair, and Meg had even accused him of caring…. Benny was right, Dean was confused.

“I swear, if I had had to sit in Lucifer’s presence for one more _second_ , I just might have snapped and stabbed him through the heart – assuming he has one,” Crowley seethed the next day as he joined Dean while he worked.

Dean turned away from the washer, blinking at the guard in surprise. “Um… what?”

He sighed, leaning against a nearby table. “It’s been a long day.”

“Alright… so, why are you complaining to me about it?”

Crowley looked at him as though he thought he was an idiot – hell, he probably did. “Because I can’t exactly talk to the other guards about this, and currently, you’re my favorite prisoner.”

“Gee, thanks,” he muttered, pulling the next basket closer to start loading it into the washer. “You do realize how kinky that sounded, right?”

He chuckled, his tired expression instantly morphing into a smirk. “Oh, of course. But the fact that _you_ took it there means you must have entertained the idea of some prisoner-and-guard not-exactly-roleplay.”

Dean glared at him. “In your dreams.”

“Oh, come now, there’s no need to play hard to get. You know you’ll enjoy it. And it would certainly improve my day.”

He rolled his eyes, turning back to his work. Yes, he was sure he _would_ enjoy it, but he was already too involved with Crowley for his liking. He didn’t need to add sex into the mix. “Sorry, Crowley, but improving your day ain’t my job.”

“Yet you do it so well,” he murmured, almost more to himself.

Dean shot him a confused look, but he decided it would probably be best not to ask. He just needed to accept that Crowley was never going to make sense to him. Yeah, like that was ever going to work. He hated unsolved mysteries, and these inconsistencies in Crowley were really eating at him.

“Mr. MacLeod,” a cool voice spoke from the doorway, and both Dean and Crowley’s heads snapped towards the new arrival.

“Lucifer.” Crowley immediately straightened up, nodding his head respectfully towards the warden.

Dean glanced nervously between the two of them, a bad feeling twisting in the pit of his stomach as he caught Lucifer’s suspicious gaze.

“And what exactly are you doing?” Lucifer demanded.

“Just checking on Winchester here,” Crowley said smoothly. “Making sure he’s doing his work properly. He seems to think that because of his injuries he can slack off.”

“Hmm… that so?” he asked skeptically.

As Lucifer’s attention was focused on Crowley, Dean acted without thinking. He tore at the stitches on his left arm until he was bleeding a fair amount, then shifted slightly to ensure that the injury was visible to Lucifer. “I’m not slacking, he muttered, effectively gaining the warden’s attention.

Lucifer’s eyes flickered down to the reopened wound, and a cruel smile twisted up his lips. There was a gleeful glint in his eyes as his gaze returned to Crowley. “Carry on.” With that, he turned and left the room, leaving Crowley blinking after him in surprise.

“Well, that was-” Crowley stopped mid-speech as he turned and saw the blood on Dean’s arm. His wide eyes moved from the injury to Dean’s face in disbelief.

Dean cleared his throat uncomfortably as the weight of what he had just done settled on him. He had just injured himself to get Crowley out from under Lucifer’s scrutinizing gaze. Benny was right. It might not be as easy to convince Crowley that he hated him as he thought. “He suspects you for Alastair, doesn’t he?” he guessed.

“He _did,_ thanks in no small part to our favorite nurse. But if he thinks I’m beating on you, too…” He frowned, shaking his head slightly. “Not that I’m not grateful, but… why?”

He shrugged, looking away from him. “Didn’t know what would happen to our deal if you lost your job,” he lied. “Didn’t want to risk it.” There, hopefully that would do the trick and he hadn’t screwed things up too much.

Crowley huffed a small laugh as he took a step closer. “Let me see your arm,” he said softly.

Dean was ready to refuse, to just turn back to his work and ignore the throbbing pain and the blood running down his skin, but he was already lifting his arm, bringing it to rest in Crowley’s outstretched hand. He didn’t know why his heart rate was suddenly increasing as the guard scrutinized his injury, why he was having to remind himself to breath evenly.

“I don’t suppose you want to go to the infirmary,” Crowley finally broke the silence, his gaze moving up to meet Dean’s.

Dean looked away, unsure of what he would see on his face. “No, I’ll be fine,” he said quickly. He attempted to turn away, but Crowley still had ahold of his arm. “I should probably just get back to work – wouldn’t want anyone to think I’m using my injury to slack off.”

“Nonsense. It’s nearly rec time now, anyway. Let me patch you up.” Dean looked at him in surprise, and he smiled. “It’s the least I can do.”

Part of Dean wanted to put up more of a fight, but Crowley was insistent. Before he could even start to argue, the guard had left the room to get the supplies he needed. When he returned, he immediately navigated Dean to sit on the table, then hoisted himself up beside him and started tending to the wound, cleaning and wrapping it.

“Next time you want to injure yourself to save my job,” Crowley voiced after a few minutes of working in silence. “Try not to rip so many stitches.”

Dean rolled his eyes. “Oh, come on. I’m pretty sure you wouldn’t go easy on me,” he said with a slight smirk.

Crowley’s eyes flickered up to meet his, an answering smirk on his lips. “I most certainly would not. And I’d bet you’d like it.”

“I bet I wouldn’t be alone in that.” He really needed to shut up. If he wanted to flirt, he should save it for Benny – that would be far safer.

But Crowley’s tongue was darting out over his lips, and _damn,_ Dean couldn’t look away. “I can guarantee you wouldn’t be,” he said in a low voice as he leaned in closer. And Dean should really be pulling away, but instead he was frozen in place, his eyes locked on Crowley’s lips as they moved closer….

“Dean.”

Dean and Crowley sprang apart, turning to where Castiel stood in the doorway, frowning.

“Uh, h-hey Cas,” Dean stammered, sure his cheeks were probably bright red. His eyes flickered briefly to Crowley, whose expression was a cross between irritated and amused.

“I went to the rec room, but you were not there,” Castiel said as he stepped into the room, looking between Dean and Crowley, his gaze uncertain.

“Uh, yeah…. I, uh, busted some stitches while working, so Crowley was just patching me up.” He held up his wrapped arm as evidence.

“I see….” His narrowed eyes rested on Crowley. “Funny, that was not what it looked like.”

Crowley arched an eyebrow as he jumped down from the table. “Oh? And what did it look like?”

Deciding that he didn’t want to hear the answer to that question, Dean hastened to speak. “You were looking for me, Cas?” he asked as he got to his feet.

“Yes.” Castiel’s expression relaxed slightly as he turned to look at him. “Your brother is here to see you.”

A weight settled in his stomach. Right. Sam. Sam who was bringing him what he needed to get out of his deal with Crowley. Crowley who he had nearly just… but it didn’t matter. He didn’t know what the hell had come over him a few seconds ago, but what he did know was that he needed out of this deal, one way or another.

“Great,” he said as enthusiastically as he could manage as he left Crowley’s side to walk over to Castiel. “Thanks for the help, Crowley,” he called over his shoulder.

“My pleasure,” he replied.

Castiel shot the other guard one last distrusting look, then turned and escorted Dean from the room. They walked in silence for a couple minutes before he spoke up. “So, what _did_ I walk in on?”

“It’s just like I said, Cas,” Dean insisted with a shrug. “I busted my stitches, and Crowley just happened to walk in and saved me a visit to the infirmary.”

He searched his face for some sign of the truth, but when it was clear that he wasn’t going to find anything, he turned forward again and they walked in silence.

Dean hoped that Castiel was going to let it go, but when they reached the door to the visitation room, the guard stopped, standing between Dean and the door. “Dean, you should know that Crowley only cares for people as far as what they can do for him. He uses people to serve his own purposes, and that’s all.”

Dean blinked at him in surprise. “Yeah, I know that.” He wasn’t stupid. He knew that Crowley didn’t give a damn about him aside from the information he got for him. Even if sometimes it seemed that it might be more than that, he knew better. And that was just fine by him. He didn’t care what Crowley thought of him.

Castiel nodded. “I think you should be sure to remember it.” With that, he opened the door and led Dean into the room.

Dean smiled, pushing his conversation with Castiel and everything that had happened with Crowley aside, as he took his seat across from his little brother and picked up the phone. “Thanks for coming, Sammy.”

“Of course,” Sam said immediately, his eyebrows furrowed in concern. “But what’s this about, Dean?”

“I just want to see something.” His eyes flickered down to where his dad’s journal sat in from of Sam. “Could you open to the entries shortly after mom died?”

“Why do you-?”

“Please.” He caught and held Sam’s gaze, his eyes pleading for him to not argue for once. “I can’t explain now. You just have to trust me.”

Sam held eye-contact with him for a couple more seconds before he nodded with a sigh. “Alright.” He riffled through the journal a bit before laying it out flat and turning it to face Dean.

He scanned over the entries briefly, shaking his head slightly. “Turn the page…. Turn…. Turn.” He breathed in deeply as he finally found what he was looking for. “That’s it.” He looked back up at Sam. “I need you to get me a picture of this page.”

Sam frowned down at the entry before he slowly looked back up at his brother, his eyes worried. “Is this about what I think it is?”

“Yeah,” he nodded. There was no point in lying to him, it was all practically spelled out for him on the page.

“Are you okay? Is he-?”

“He’s not doing anything,” Dean cut him off firmly. “I’m fine. I just need that picture. And then I need you to keep the journal safe – don’t let anyone see this.”

“I don’t understand, Dean.” Sam shook his head slightly.

“I know. And I’m sorry. I just need you to do this for me.”

“Alright,” he sighed. “I’ll give Cas the picture.”

“Don’t let him see it,” Dean said severely.

“You don’t trust Cas now?” Sam demanded, frowning.

“No, I trust him, I just… he can’t know about this.”

“Fine,” he muttered, clearly unhappy, but resigned to do as Dean asked.

“Thank you,” Dean said fervently. By this time tomorrow, his problems with Crowley should be solved. Or at least, he’d be out of his deal. After today, though; he wasn’t sure that that would put a stop to all his problems with the guard.


	13. Blackmail

As Dean took a seat in the cafeteria the next day, he was buzzing with nerves at what he was planning to do later that day. Any hope that his expression, at least, was composed vanished as Benny kicked him beneath the table, giving him a pointed look.

“Piece of advice,” he said in a low voice. “If you’re goin’ through with this – you need to be all in or all out. Otherwise, it won’t pan out so well.”

He nodded, taking a deep breath. He knew he was right. Crowley could read people better than just about anyone else Dean knew. If he showed even the slightest hesitation, he was done for. If Crowley caught him in a lie… well, it would just probably be safest to aim to be as honest as possible.

“Believe me, I’m all in,” he muttered. He patted his pocket subconsciously, feeling the outline of the envelope that Castiel had given him that morning. A quick peak inside had shown that Sam had come through for him – not that he’d had any doubt that he would.

“I certainly hope so. You haven’t really gotten a taste of Crowley’s bad side yet, and it ain’t pretty.”

“I’ll deal,” Dean said confidently. Hell, it was probably a good thing that he’d be off Crowley’s good side before he got too comfy there. He didn’t want to risk forgetting what Crowley’s real motivation to be nice to him was. It would be better to be reminded of the worst in him. “Besides, if all goes to plan, he won’t risk doing anything to me.”

“And if it doesn’t, you won’t get out of your deal, and you’ll be even more screwed than you already are,” Benny added wryly.

He sighed. “Thanks for the vote of confidence.”

“Look, I’m not sayin’ you don’t have a shot – because I’m starting to think you might actually have a pretty good one. I just think you should be prepared for all possible outcomes.”

“And I am,” Dean assured him. “But trust me, this will…” He trailed off as he caught sight of Crowley strolling down the aisle between the tables, heading in their direction. He caught his eye and gave him a meaningful look that hopefully translated to something along the lines of, _‘I’ve got some information for you – let’s talk later.’_ Judging by the guard’s slight smirk and nod as he passed by him, he was successful.

Dean breathed out a breath that he hadn’t realized he was holding. Well, everything was in place. There was no turning back now. Not that he had considered turning back, but even if he had, he was past the point of no return. He was going to blackmail the king of blackmail.

His nerves only increased as the day wore on. He was sure that at any moment, Crowley would corner him, asking what he had for him, and he wished that it would just happen already. Whatever direction their conversation would end up taking, Dean was pretty sure at this point that the suspense was worse.

As he worked that day, he repeated what he was planning to say over and over again in his head, trying to predict how Crowley might respond. Would he lash out? Would he find a way to hold something else over his head – something he could threaten him with? Or would he believe he was bluffing? Dean really didn’t want to go to Lucifer with this, but if he had to… well, honestly he wasn’t sure what he would do. Surely Crowley wouldn’t want to take that risk, though. Right?

When Crowley didn’t come see him while he was working, he started to panic. Had he somehow found out what Dean was trying to do? Was he figuring out a way to stop him? But how could he have possibly found out? Dean had been so careful in his preparations. But there was no telling what kinds of resources Crowley had at his disposal. It certainly wasn’t impossible for him to have found out. And if he had… what would happen now? Nothing good, that was for sure. Dean cursed himself for being so careless.

Five minutes into rec time, Dean heard a familiar voice behind him. “Winchester.”

He swallowed thickly as he turned around. One way or another, this was it. He didn’t say anything as he met Crowley’s gaze, quickly schooling his expression.

“Don’t think I didn’t see that. I think you ought to come with me.” He grabbed Dean roughly by the arm, towing him into the hallway. Dean, and anyone else who might have overheard Crowley, knew full well that he hadn’t seen him do anything, but the attempt at an excuse was all a guard needed to pull a prisoner aside here – especially when that prisoner was Dean Winchester.

Crowley’s grip on Dean relaxed as they entered the hall, and he felt himself relax in turn. Surely, if he knew what Dean was up to, he wouldn’t be showing him any form of kindness.

Dean was regaining his confidence in what was about to go down as Crowley led him a short way down the hall and through the door to the guards’ bathroom. He released his hold on Dean’s arm and turned to lock the door, while Dean took a few steps into the room to put some distance between them before turning to face him, careful not to let any apprehension he felt show on his face.

“So,” Crowley turned back to face Dean, his expression eager. “What have you got for me?”

“It’s information on a guard, actually – not a prisoner,” Dean began, the pounding in his chest contradicting his confident tone and expression.

He raised his eyebrows. “Even better. Well, are you trying to build up suspense?”

He took a deep breath as he pulled the envelope from his pocket, unfolded it, and handed it to Crowley with a surprisingly steady hand. The guard took it curiously, opening it up and pulling out the picture. Dean knew what he would read on it:

_After weeks of searching for answers, I finally found someone who could provide. A guard from the prison Mary had visited before her death – Crowley MacLeod. The guy’s a scumbag but he got me what I needed. I’m not proud of what I had to do for the information, but it was worth it. Azazel. That is the name of Mary’s murderer, and Crowley gave me everything I need to put him away for good. And with what I’ve learned, it’s no longer just about revenge – it’s about protecting my boys. He might still come back for Sam, and I need to get him behind bars before that happens._

Crowley’s enthusiastic curiosity faded from his face as he read the journal entry in the picture. Dread, irritation, fear, and anger all flashed across his face in quick succession, but when he looked up at Dean, his face was expressionless. “And here I had thought we were having a moment yesterday.”

“We were,” Dean admitted. It was better to be honest, after all; he’d be more convincing that way. “But that doesn’t change that I want out.”

“So, you thought that – what? You’d show me this picture -” He waved the picture in the air to illustrate his point. “- and then I’d agree to keep your and Castiel’s secret whilst you no longer have to work for me?”

He shrugged casually. “I mean, assuming you don’t want me to show the journal in that picture to Lucifer, yeah.”

He expected to see a return of the anger, but instead Crowley looked more amused than anything. “Darling, I admire your attempt, but this is just writing on a page. Why would Lucifer believe it?”

“Oh, I don’t know, maybe because Azazel and Alastair were his favorites, so if they were looking for answers on where Dad got his information, I’m guessing Lucifer is, too. And he’s already suspicious of you getting Alastair arrested – so, do you really think he would question this?”

His eyes narrowed slightly. “Perhaps not, but you’d still be stupid to follow through.”

Dean raised his eyebrows. “And why’s that?” Although he had a pretty good guess as to what Crowley was getting at, and he already had his answer prepared.

Crowley took a step closer. “Because if I go down,” he murmured in a low voice. “You can be damn sure that I’m taking Castiel down with me. And you can’t have that, now can you?”

He didn’t so much as bat an eye at the threat. “I doubt anyone will listen to you after you officially become the most hated guard in this place – they’d just think you were trying one last desperate play to save your job. But on the off chance that they do believe you – I know what Cas would have me do. He’d rather this prison have neither of you than for you to be a guard here. And I’m willing to take that risk, if it means a return of my free will.”

Crowley searched his face, and Dean was careful to keep his expression resolute. He needed Crowley to believe that he wouldn’t back down on this. And he _wouldn’t._ He needed out of this deal.

“I could call your bluff,” Crowley said softly. “You bled for me yesterday – all to convince Lucifer that I had nothing to do with getting a guard arrested. And now you expect me to believe that you’re going to convince him of the exact opposite?”

“Yes,” he said firmly. “I needed Lucifer to doubt you on my terms – if things went downhill yesterday, it’d be out of my control. I couldn’t let that happen. So, I did what I had to do.”

He blinked, clearly caught off guard by Dean’s well-prepared excuse. He studied him for a few moments more before he inexplicably chuckled, a smile pulling up the corners of his lips. “Alright. You’re off the hook, so long as you make sure this journal stays away from any prying eyes.”

Dean couldn’t keep the surprise from his face at Crowley’s sudden light-hearted tone. “Don’t worry,” he assured him with only slight confusion slipping into his tone. “It’s safe – no one will be getting to it. And you can destroy that picture yourself, for your own piece of mind.”

“Appreciate it,” Crowley murmured, slipping the picture into his pocket before meeting Dean’s gaze once again with a smirk.

He cleared his throat. “Uh… don’t take this the wrong way, but I figured that you’d be more – I dunno – pissed.”

“I’m disappointed,” he allowed with a small shrug. “But no one has ever succeeded in blackmailing me before, and very few have been stupid enough to even try. I’m continually impressed by you, Dean Winchester. I just wish that didn’t mean I have to lose you. You’re a natural at this line of work.”

Dean’s gut reaction was to protest – this kind of work was below him, and there was no way that he was a natural. Except… blackmailing Crowley had been surprisingly easy. Even the information that he had gotten from Gordon hadn’t been difficult to get, and he had gotten the impression that he wasn’t the kind of guy who normally shared his story so openly. But what was more than that… it felt _good._ He had gotten valuable information from someone who kept to himself, and he had managed to blackmail _Crowley,_ of all people _._ He felt… powerful, and a bit smug, too. Maybe being a mechanic had been the wrong line of work for him. Of course, he didn’t actually believe that, but it was an interesting thought to entertain, nonetheless.

“Maybe,” he realized he had to admit. “But that doesn’t mean I’m about to tolerate being your bitch.”

Crowley looked thoughtful for a second before he took another step forward. “No, I suppose that doesn’t fit you, does it?”

“Nope.” He popped the ‘p’ with a smirk.

He nodded as he took one more step closer, the movement bringing him close enough so that he didn’t have to extend his arm much to rest his hand on Dean’s hip. Dammit, how had he gotten so close? Dean wasn’t sure what his face was doing as he glanced down to the hand, then back up at Crowley’s face, but he was pretty sure he was an open book.

“Perhaps I can make it up to you?” Crowley offered in a low voice, and the look in his eyes when the met Dean’s was enough to pin him to the spot.

He forced himself to take a deep breath, wishing his heart would quiet down so that he could _think._ “I’m not getting in any deeper with you,” he finally managed to say, his voice shaking just slightly.

Crowley’s eyes were laughing as he arched an eyebrow at him. “But you’re not in with me, anymore. I could be in you, though.”

Oh, _fuck._ He licked his lips, and Crowley’s eyes darted down to follow the motion. “I…” There definitely had to be a good reason why they shouldn’t be doing this, but for the life of him, he couldn’t think of what it was.

“Oh, come now.” He moved still closer, pressing his body up against Dean’s in a way that served to further shut down his thought processes. “You seemed to want it yesterday. Or was that just an attempt to knock me off my game today?”

“No,” he answered truthfully before even stopping to consider the question. He was leaning into his touch now, and this was definitely a _bad idea._ But…

“So?” Crowley pressed – both with his question and his body.

Dean swallowed thickly. Oh, fuck it – he was in prison with no chance at getting out, what was the point in being careful? So, he kissed him.

He had control of the kiss for all of about five seconds before Crowley took over – not that he minded in the slightest. Crowley’s lips against his were hard, demanding, passionate, and sensuous all at once. He felt his back collide with the wall, but he hardly noticed.

He might not have the clearest mind at the moment, but he decided that he had made the right choice. Crowley was right – he wasn’t involved with him anymore, so what was the harm?


	14. What Now?

Dean cringed slightly as he sat down on the hard, metal chair. He hadn’t been this sore in a while, but Crowley hadn’t exactly been gentle, nor was he anywhere close to average. Dean’s cock twitched at the memory, and he quickly shoved those thoughts to the back of his mind. He did _not_ need to get hard at breakfast and be unable to do anything about it for the rest of the day.

He turned his attention to Benny to see him smirking at him.

“Shut up,” he muttered.

“I didn’t say anything,” Benny protested.

Last night, had given his cellmate a brief rundown of what had happened, save for the part about him having sex with Crowley. But judging from the look on his face now, he had worked that out for himself. “No, but you’re thinking it.”

He arched an eyebrow, his smile amused. “Thinking what?”

Dean sighed exasperatedly before fixing him with a glare. “Fine, just say it,” he snapped. Having it out there would be better than Benny silently laughing at him, at least.

“Don’t know what me to say. That I could tell last night there was something you were keepin’ from me? Or that it’s clear that someone fucked you thoroughly, and I think I’d remember it, if it was me? Or perhaps that Crowley keeps looking at you like you’re a piece of meat? He hardly seems upset that you got one over on him.”

He had managed to keep his expression controlled until Benny’s last point, at which he couldn’t stop the blush from forming on his cheeks. He had felt Crowley’s eyes on him from the moment he’d entered the cafeteria, but he hadn’t been entirely sure that it wasn’t just his imagination – apparently, it wasn’t. He resisted the urge to look over at him, instead keeping his gaze fixed on Benny as he cleared his throat. “You done?”

He shook his head in disbelief. “So, the guy’s no longer blackmailing you, but now you’re sleepin’ with him?”

Dean sighed, his eyes dropping down to his tray. “Yeah. I know, I’m a total idiot.”

Benny didn’t comment for a couple of seconds. “Was he good?” he eventually asked.

“Uh…” He bit his lip. He didn’t want to use the words ‘best sex I’ve ever had’ with someone else that he had slept with, but judging from Benny’s expression when he glanced up at him, he got the picture.

“Damn,” he muttered, sounding almost impressed. “Think it’s goin’ to happen again?”

“I…” Dean frowned. He honestly wasn’t sure. Crowley hadn’t really given him much to go on – sure, he had been extremely enthusiastic, but afterwards, he had simply said that he should escort Dean back to the rec room, and then he did as much. He had done absolutely nothing to indicate that he would like to have sex with Dean ever again. Maybe he’d just wanted to get it out of his system. Or maybe it hadn’t been as good as he had thought it would be. That thought bothered him more than it should, considering that it was only Crowley. “I have no idea,” he admitted.

“Do you want it to?” Benny pressed, his smirk back in place.

“I… I don’t know,” he sighed. “I mean, it was great, but it’s _Crowley.”_ He shook his head. “What do you think I should do?”

“Well, on the one hand, the guy’s an asshole. On the other, any guy who makes you look like that is clearly worth something.”

Dean rolled his eyes. “Thanks for the help.”

“Any time, brother,” he replied with a charming smile.

They were almost done with breakfast when Dean thought to ask, “Hey… this doesn’t bother you, does it?”

Benny frowned up at him. “What doesn’t bother me?”

“Uh, you know… me and Crowley hooking up,” he said awkwardly.

He laughed. “You aren’t goin’ to be hurt if I say no, are you?”

“No,” Dean said, the corners of his lips tugging up into a grin. “Relieved, actually.”

“Well, then – no. I like you, Dean, but not enough to get jealous.”

He nodded. “Glad to hear it.”

“Crowley, on the other hand, might feel differently,” he commented nonchalantly. “He strikes me as the possessive type.”

“Well, he certainly didn’t seem it last night,” Dean muttered, his words coming out more bitter than he had intended.

Benny chuckled. “If you like, I can plant one on you now – that might get a reaction out of him.”

He shook his head. “I don’t – I don’t need a reaction. I don’t give a damn what he thinks.”

“Sure you don’t, chief.” His eyes were sparkling with amusement.

Dean glared at him. “I don’t,” he repeated firmly.

And he didn’t. Honestly. Last night with Crowley had been one big mistake. Sure, it had been an exceptionally enjoyable mistake, but a mistake all the same. And yes, maybe a part of him wanted to repeat it – a _small_ part – but that didn’t mean anything. It had been the best sex of his life, of course he wouldn’t mind reliving it – it had nothing to do with Crowley himself. And it would probably never happen again, anyway, so there was no point in dwelling on it. It had been a fantastic one-night stand, but that was it. Crowley probably had much better things to focus his attention on than some prisoner who had miraculously succeeded in screwing him over. The novelty factor was probably the only reason he had initiated anything, in the first place, and that had probably already worn off by now. And Dean was just fine with that. He was better off with Crowley as nothing more than a background character in his life.

So, at work that day, Dean pretended that the reason his gaze kept moving towards the door was to ensure that no guards were about to get the drop on him – not because he was half expecting that Crowley might be walking in at any second. He pretended that his jitteriness was from nerves at no longer being under Crowley’s protection – not because his mind kept wanting to play scenarios of Crowley coming in and distracting him thoroughly from his work. All in all, he did a pretty good job of convincing himself. Especially when it became evident that his excuses were more likely to happen than what he was denying.

He had just looked towards the doorway, looking for the appearance of guards who weren’t Crowley, when Drexel entered the room.

“You seem to be recovering nicely,” the guard said casually as he approached.

Dean hadn’t had much interaction with Drexel, but from what he knew about him, he was in a constant state of sucking up to Lucifer. He wasn’t dreadfully brutal in his beatings, but he was precise.  More importantly, he wasn’t as naturally inclined to beating any prisoner he could get his hands on as most of the guards here were, but he would target the prisoners he knew Lucifer hated the most if he felt they were getting off too easy. How on earth anyone could think Dean was getting off _easy,_ though, he had no idea. Still, if he played his cards right, he might be able to talk his way out of this.

“Yeah,” he scoffed, flinching slightly as he reached his arm up to open the lid of the washer. “Except for Crowley opening up my stitches five seconds after I got out of the infirmary, I’m doing great.”

“He can’t have done too much damage,” Drexel commented as he continued walking forward, his tone still disturbingly casual. “You’re still walking and talking.”

Crap. He could already tell that he wasn’t going to be able to get out of this. “Barely,” he muttered, his heart hammering as desperation clawed at him. He did _not_ want to end up back in the infirmary.

He nodded as he stepped within arm’s reach of Dean. “What do you say we fix that?”

Before Dean could do more than blink, Drexel’s hand had shot out and grabbed hold of his jumpsuit, yanking him forward and then slamming him back against the machines behind him, his head striking squarely against one of the dials.

He raised his other hand, but suddenly another hand closed around his wrist, and a cold, menacing voice spoke from behind him. “Unhand him _now.”_

Drexel jumped, his hand immediately releasing its grip on Dean’s jumpsuit as he spun around, and as Dean regained his footing, his eyes widened as they rested on his savior.

“Crowley. What seems to be the problem?” Drexel asked nervously.

Crowley released the other guard’s wrist as though it was the most disgusting thing that he had ever touched. “Dean Winchester is _mine._ No one else lays a hand on him.”

Dean was sure that his expression was just as surprised as Drexel’s. Damn. Maybe he was possessive. “I didn’t realize…” the guard said slowly. “You never even liked Azazel. Or Alastair.”

“No,” he admitted. “But it’s the principle of the matter. Apart from Gabriel, I am now the guard that has been here the longest, am I not?”

“Y-Yes,” he stammered.

“Therefore, Dean is mine. And unlike Alastair, I am not inclined to share. Understood?”

Drexel nodded hastily. “Yes, sir.”

Crowley smiled coldly. “Well, run along, then.” He turned, watching Drexel leave the room as quickly as he could without actually running. “Bloody coward,” he muttered, as soon as he was gone. He turned back to Dean, his expression softening into something akin to concern. “Are you alright?”

Dean blinked in surprise, and it took him a few seconds to recover enough to speak. “Y-Yeah.” He cleared his throat. “Thanks.”

“Of course.”

“But… why did you help me?” he couldn’t help but ask. It didn’t make any sense. Surely Crowley would want him to bear the brunt of what he had been protecting him from under their deal. “We don’t have our deal anymore.”

“I’m aware. But as I believe I’ve said before, it would be a shame to ruin your pretty face. Especially now, when I am quite enjoying the benefits to having you in one piece.” He winked.

Dean felt his cheeks heat up slightly. So, maybe it wasn’t a one-time thing, after all. “Oh,” he muttered lamely.

Crowley chuckled. “Surely you didn’t think I could possibly be done with you after just one night?”

“Well, you didn’t exactly give me anything to… go off of,” he finished quietly when he realized how heated his words were coming out.

The damage was already done, though, and Crowley was smirking victoriously. “I see…. Well, allow me to correct my mistake.” He stepped closer, his lips sliding against Dean’s. “I intend to take you every chance I get,” he murmured as he pulled away. “Unless you object of course,” he added, grinning knowingly.

Dean swallowed thickly. “No, I… don’t object,” he muttered, the truth somehow slipping out before he could pull together a convincing lie. Oh well, it was a little late for that, anyway. He had already given himself away.

“Excellent.”


	15. Final Offer

“You got your application in?”

“Yes,” Sam sighed. “Only because you had Bobby force me to fill it out. But it doesn’t mean I’m going, even if I do get accepted.”

“Dammit, Sammy.” Dean shook his head. “This has been your dream since you were a kid. You have to go.”

“A lot has changed since I was a kid, Dean,” he pointed out. “I just… Dad’s dead, you’re in prison…. He never even wanted me to go in the first place.”

“So, what? Now that he’s dead, you suddenly have the urge to do what he wanted?” Besides, the whole reason Dad hadn’t wanted Sam to go to Stanford was because he didn’t want him to be so far away – probably due to nearly having lost him as a baby – and that clearly didn’t apply anymore.

“It’s not just that,” Sam explained. “I… I feel bad leaving you here.”

“Sammy…” Dean sighed, shaking his head slightly. “Look, I’ve lost my chance to live my life. That doesn’t mean you should, too.”

“Dean-”

“I’m not finished. If you refuse to live for yourself, live for me, okay? Go live your life to the fullest to make up for the fact that I can’t. Can you do that for me?”

Sam sighed, his eyes darting down to the table in front of him. “I have to be accepted, first,” he muttered.

Dean smiled, knowing that he had victory. “And you will be.”

He looked back up at his brother, the corners of his lips pulling up slightly. “Well, if you’re right – and if I can find a way to pay for it… I’ll go.”

“Good.” He gave his brother a victorious grin.

Sam rolled his eyes. “At least you seem to be doing better.”

“I am,” Dean agreed with a nod. “I mean, it’s still prison, but things are looking up.”

“So… Crowley’s off your back?”

He had a sinking suspicion that his cheeks were turning faintly pink, and he really hoped he was wrong. “Y-Yeah.” Well, he’d been pressed against his back this morning, but that was another matter.

Sam’s eyes narrowed slightly. “Dean?” he pressed.

Dean sighed. “Everything’s fine, Sam.”

“Okay, um… I wasn’t gonna bring it up, cause I thought there’s no way, but I was talking to Cas-”

“What?” he interrupted, his eyebrows furrowing. “When were to talking to Cas?”

“You’re who got us in contact, Dean,” he pointed out. “And I know you don’t tell me everything, so it feels like that’s the only way I can really know what’s going on with you.”

“Wow,” he muttered.

“I’m worried about you, okay?” Sam said defensively. “And… and Cas said he was pretty sure he walked in on you and Crowley about to kiss a little while ago.”

Yeah, Dean’s cheeks were definitely heating up now. “You and Cas gossip like old ladies,” he grumbled.

“Hey, I didn’t believe it, at first. I told him it must not have been what it looked like. But when I mentioned Crowley just now, you got all jumpy.”

“No, I didn’t,” he protested.

“Yeah, Dean, you did,” Sam sighed. “What’s going on?”

Dean sighed, running a hand over his face. “Okay, okay. I know what Cas was talking about, and it wasn’t what it looked like. We weren’t doing anything – he was just patching me up, and Cas walked in at the wrong moment.” At least that was half true. “Things with Crowley are just… complicated.” Now, that was the truth.

His eyes narrowed. “What do you mean?”

“I mean…” He hesitated. If someone were to overhear him telling Sam that things were getting better, they wouldn’t think much of it – they would just assume he was trying to reassure his little brother – but if they heard him saying that he was actually starting to almost like Crowley (and not even just because he got him off better than anyone else could), things could get very bad for one of Dean’s new favorite guards. “That everything’s okay. I promise. There’s no need for you to worry.”

“You’ve told me that before,” Sam accused. “And yet every time I come to visit you still nearly always look like you’d been someone’s punching bag – that they’d decided to run over with their car.”

Dean rolled his eyes. “You’re just gonna have to trust me, Sammy. I’m okay.”

He sighed. “Did the journal entry-?”

“Yeah,” he quickly assured him. And that wasn’t even a lie. The journal entry _had_ helped him; it had done just what it was supposed to do. He just hadn’t anticipated where things would go next. “Like I said, I’m all good.”

Sam nodded, clearly not entirely convinced, but willing to let it go. “Okay.”

“Time to wrap it up, Dean-o,” Gabriel said as he walked over to them.

Dean nodded at him, then turned back to his brother. “Well, I gotta get going.”

“Right,” Sam sighed. “Oh, by the way, Bobby said he’d try to come by tomorrow. He wanted to today, but Rufus needed his help with something.”

“It’s cool. See ya, Sammy.”

“Yeah. See ya,” he replied sadly.

Dean had always been better about ignoring his own feelings than ignoring Sam’s, and so the most painful part about saying goodbye to him this and every other time wasn’t the act himself, but was the sorrow in his brother’s eyes. He could deal with his own loneliness, but he couldn’t deal with Sam’s. Still, he had no choice but to force himself to tear his eyes away as he followed Gabriel from the room.

“He really looks up to you, doesn’t he?” Gabriel commented as they walked.

“Yeah. He does.” _Even though he shouldn’t,_ he added silently. He was in prison, for crying out loud. But he supposed that Sam didn’t have it much better. He had been dealt a hand he didn’t deserve. He had lost just about everything, and now he didn’t even think he deserved to live his dream. And here Dean was, adding to his pain, and unable to do anything about it. The weight of his imprisonment was suddenly crashing down upon him, the good mood he’d started the day with fading entirely.

And then Dean caught sight of the one person who somehow always seemed to be able to take his mind off his problems and put him at ease. He wasn’t entirely sure when he had realized the effect he had on him, but he could already feel a slight hint of relief just at seeing him. “Crowley,” he found himself saying, getting the guards attention.

Crowley turned around as Gabriel came to a surprised stop.

“Hello, squirrel,” he said with a smile as he walked back down the hall towards them. “Gabriel,” he nodded to the other guard.

“Heya, Crowls.” Gabriel look curiously between the two of them. “Something going on here?”

Crowley met Dean’s eyes, seeing the desperate plea in them – the plea for Crowley to help him feel like maybe he wasn’t a total piece of crap for at least five minutes. “I told Dean this morning that I needed to have a private word with him later,” he lied smoothly, turning back to Gabriel.

“Really?” He crossed his arms over his chest skeptically. “What about?”

“You never did understand the word ‘private’, did you?” he complained.

“Nope.” He popped the ‘p’ with a smile. “Come on, you gotta give me something sweet to satiate me.”

“Don’t I know it,” Crowley muttered, good-natured irritation coloring his voice. “Fine. I happened across some information on the company of a certain late business-owner that I thought he might be interested in.”

Gabriel arched an eyebrow. “That so? Cause see, a little bird told me that Dean’s your own personal punching bag now. You won’t even let anyone else touch him.”

Crowley didn’t say anything; he just smirked slightly. It was what he wanted everyone to think, after all.

“Only,” Gabriel continued, his eyes dancing. “If that were really the case, why would Dean get your attention? Why would he seem to _want_ to be alone with you?”

Dean’s stomach twisted into a knot as he realized how much he had just messed up. “Gabriel-” he started, but the guard wasn’t done.

“Of course, it doesn’t take much to figure it out. And that _would_ explain why you haven’t booty called me in over a month.”

Crowley’s eyes were narrowed by this point. Meanwhile, Dean had completely lost what he was going to say and was looking between the two of them with his mouth slightly agape.

“Or maybe it’s because I’m tired of you eating all the sweets in my house,” Crowley suggested, his tone still casual. “And as for Dean… maybe he’s a masochist?”

Gabriel rolled his eyes. “You don’t really expect me to believe that, do you?”

“Gabe,” Dean said, recovering from his shock. “Please, _please,_ don’t tell your brother – either of them,” he added hastily, remembering that he needed to include Lucifer in that request.

“Of course I won’t,” he said indignantly, turning to Dean. “Or have you forgotten that I’m the only person here who actually likes the both of you?”

“I know, but-”

“But you also have the propensity for stirring up trouble,” Crowley finished for him. “Doesn’t hurt to play it safe.”

Gabriel rolled his eyes as he straightened up, resuming an at least semi-professional demeanor. “Crowley, you can take Mr. Winchester from here. Don’t do anything I wouldn’t do,” he added with a wink.

He sighed, turning to Dean as the other guard walked away. “I am never going to hear the end of this. Come on.” He turned and continued on down the hall, Dean falling into step beside him.

“Do you two really…?” He trailed off, suddenly unsure if he wanted to hear the answer.

“Fuck?” Crowley guessed anyway. “We have. I believe you are familiar with the concept of friends with benefits, are you not?” He looked at him pointedly, and Dean wondered how he could know about him and Benny. He didn’t feel like asking, at the moment, though.

“Yeah,” he merely said instead, his voice subdued.

“What’s the matter?” He arched an eyebrow, smirking slightly. “Jealous?”

“No,” Dean denied with a roll of his eyes.

“Good. Because like Gabriel said, we haven’t slept together since before you and I started up. And it meant nothing.”

Dean was about to point out that what they were doing meant nothing, too, but before he could, Crowley opened the door to a storage closet and pulled him inside.

“So, once wasn’t enough for you today, was it?” Crowley teased as he pulled the door shut.

“It’s not that,” Dean sighed. Honestly, he wasn’t even sure that he wanted sex. He just needed to be close to someone. And as for why the person that it was easiest for him to be close to was Crowley, he didn’t want to look too closely at.

The guard frowned. “What’s wrong, Dean?” He reached out, pulling him in close, his hands trailing from his sides to his back.

“I dunno, I just… prison’s getting to me, I guess. I mean, before there was enough crap to keep my mind occupied, but now things are peaceful – and I’m glad for that – but…”

“But prison is a punishment for a reason.” Crowley nodded as he smoothed a hand down Dean’s back. He gave a small sigh. “If only someone could get you out.”

Dean went still in his arms, suspicion creeping in. “What do you mean?” he asked slowly.

“I was being honest back there. I found evidence that Dick Roman was guilty of everything you and your brother claimed. That should be enough to clear your name.”

His heart was pounding frantically, feelings of hope and betrayal waring inside him. Finally, the betrayal won over, and he pushed away. “And let me guess,” he said coolly. “You’ll turn over the evidence if I agree to work for you.”

“Naturally,” Crowley shrugged.

Dean shook his head, backing to the far side of the closet. “You… You’ve just been buying time, that’s all this has been about.”

“Not at all.” He frowned, taking a step forward. “I wanted this. I promise you, nothing I’ve said to you has been a lie.”

He rolled his eyes. “So, you’re an honest asshole. Great. No deal.”

“But you want to be free,” Crowley pointed out gently.

“Of course I do, but not at a price. I already told you, I don’t care what you’re offering – I won’t tolerate being your bitch.”

He shook his head. “That’s not what I’m suggesting.”

“Oh?” Dean pressed skeptically.

“I have a small group of people who work for me outside this prison,” he explained. “Gathering valuable information, utilizing it gain valuable resources – be it money, connections, more information…. Everyone is compensated extremely well, I assure you.”

He narrowed his eyes, though admittedly, he was a little intrigued. “So, why work here?”

“Prisoners are abounding with information, and it’s often almost too easy to get it from them. Also, the cheapest recruits are the most desperate ones, and the most desperate ones are often behind bars. So, I test them out in here, and if they’re good enough-”

“You’ll do what you’re doing now,” Dean finished for him, everything clicking into place. He had known that there was more to Crowley and what he was doing in here than met the eye, and this certainly answered a good many of his questions about the guard.

“Except that you are by no means cheap,” Crowley pointed out. “So. What can I do to get you to work for me?”

He blinked. “What?”

“Anything you want, Dean.” He spread his hands out in front of him, illustrating his offer. “If it’s in my power, it’s yours.”

Dean would’ve taken another step back in shock if he hadn’t already had his back to the wall. An open-ended offer from someone with a shitload connections and resources, all to get him to work for him? “Why?”

“Because I see potential in you, along with… other appeal.” He smirked as his gaze flickered over his body. “I think you would be a valuable asset, we work well together, and I enjoy your company. I know as well as anybody that it’s bad form in a negotiation to show how much you want something, but frankly, I don’t care how high of a price I have to pay to have you. You deserve it.”

He swallowed thickly. He had never felt so wanted in his life, but as much as that made him want to give in, he had to at least try to stand his ground. “Well, that’s… touching, but I don’t want anything from you.”

“Really?” Crowley arched an eyebrow skeptically. “I know that Castiel has been sending money to that brother you’re so fond of. Cute, but I can do so much more. He wants to go to Stanford, does he not? I have a connection there. I can _guarantee_ that he gets a full ride.”

Dean’s breath left him in a huff. A full ride to Stanford? And Sam had promised him he’d go if he got accepted, if he could pay for it. And dammit, he deserved that.

He was sure that his eagerness was written clearly across his face, sure that Crowley knew he had him. So, he was surprised when the guard asked, “Now, what else can I do for you?”

He thought frantically. If he could demand anything, he was damned sure going to make the most of it. “You’ll make sure he has plenty of money. That he never has to struggle.”

“Of course,” Crowley agreed with a smile. “Anything else?”

“You’ll protect Castiel’s job. To the best of your ability, you’ll make sure he doesn’t get fired.”

He sighed. “I suppose I should’ve seen that one coming. That all, then?”

Dean thought for a couple seconds, then shook his head. “Benny.”

Crowley blinked. “What?”

“My cellmate. I want him freed, too.”

“Are you…?” He sighed irritably. “I can try to get him out on parole, but I can’t promise anything.”

“Just do what you can,” Dean allowed. “And there’s one more thing.”

“Of course there is,” he muttered.

“I want some say in what I do. I am not just blindly following your orders.”

“I never expected you to,” Crowley said, the corners of his lips quirking up again. “I want you at my right hand – leading alongside me.”

That brought Dean up short. “You… what?”

“Your potential is already wasted in here, darling. I’m not about to waste it out there.”

“Well… okay then,” he said for lack of anything better to say.

Crowley chuckled, extending his arms out to Dean, who stepped forward, allowing Crowley to pull him into a kiss. “Feeling better?” he murmured against his lips.

“Yeah,” Dean admitted. “Just don’t let it go to your head.”

“Too late.” He spun them around, pressing Dean’s back against the wall.

Despite himself, Dean laughed. He reached out to cup the back of Crowley’s head, pulling him into another kiss.


	16. Freedom

“Oh, Baby, I’ve missed you,” Dean said fondly, rubbing the steering wheel of the ’67 Impala as he pulled out of the parking lot, AC/DC’s ‘Back in Black’ blasting through the speakers. Even with how desperately he had been yearning for freedom – these past several weeks, especially – he hadn’t anticipated just how _sweet_ it would feel. He was able to breath fresh air, drive wherever he wanted, spend his time as he saw fit. And currently, he saw fit to celebrate his freedom, drink in hand, alongside Sam and Bobby.

As soon as the news of the evidence against Dick Roman had gone public, Sam and Bobby had come to visit him, looking happier than he had seen either of them in a long while. Of course, clearing his name had been a long, drawn out ordeal – far too long, in Dean’s opinion – but Crowley had come through for him, as promised. As soon as his release had been finalized, Sam had driven the Impala to pick him up, tossing him the keys without having to ask if he wanted to drive.

So, now Sam was relaxing in the passenger’s seat, rolling his eyes, though he was still unable to wipe the wide smile from his face. “You want me to leave you two alone?”

“Hey!” He snapped. “You have lost your right to comment on her.”

“What?” He shook his head incredulously. “Seriously, Dean? It was just an iPod jack.”

“You can’t mess with perfection, Sammy,” Dean insisted.

“You know, it doesn’t hurt to move on from cassette tapes.”

“You shut your mouth!”

Sam held up his hands in surrender. “Fine. Whatever.” He paused as he dropped his hands. “You sure your release is finalized? They won’t take you back?”

Dean shot him a glare. “Thanks, Sam. I missed you, too. Though… they probably would.” He couldn’t imagine that Lucifer was too happy about his release.

He pretended to consider it. “Nah, I’ll deal. It’s not like I’ll have to put up with you for too long.”

He frowned, feigning innocence. “What d’you mean?”

“Well… I’m leaving for Stanford at the end of this month.”

Dean’s eyes went wide in an effective portrayal of surprised excitement. “You got in?”

“Yeah.” Sam smiled excitedly. “I wanted to wait till I could tell you the news without a pane of glass between us.”

He had figured that that had been the case when Crowley told him that Stanford had mailed out the acceptance letter, yet Sam had continued to not say anything about it.

“That’s awesome, Sammy!” he exclaimed. “I knew you could do it!”

“I know. And it’s not that I thought I _wouldn’t_ get in, but…” He shook his head, his expression slightly awed. “I got a full ride, Dean. I don’t know how I managed to swing that.”

“Who cares! You’re going to your dream school and it’s paid for. Looks like we’ve got two things to celebrate tonight.”

“Yeah, I guess so,” Sam agreed with a smile. “I just wish I didn’t have to leave so soon after you getting out.”

Dean shrugged. “It’s cool. I’ll still get to see you on your breaks, right?” He shot him a stern look, making it clear that this was not up for negotiation.

“Of course. I’ll be up whenever I can.”

“Good,” he said with satisfaction.

 A few seconds passed in content silence, both brothers enjoying being together again, before Sam spoke up again. “I think it’ll be good for Bobby to have you around after I leave for school – pretty sure he’s gotten used to having someone around the house.”

Dean frowned slightly. “Yeah… about that…” He took a deep breath, unsure of how to break it to him that he had no intention to move in with him and Bobby.

“You’re not staying at Bobby’s,” he realized, his smile slipping.

“No,” he sighed. “I just… I need to be on my own. Prison changed me, I – I can feel it. And I just can’t bring that home to you guys.” And more importantly, the last thing he wanted was for Sam and Bobby to find out about the work that he was doing with Crowley. Which was why he had already found different living arrangements, courtesy of Crowley, of course.

“We don’t care about that, Dean,” Sam protested.

“I know you don’t. But… it’s just what I need, Sammy.”

“Yeah… okay,” he muttered sadly.

Damn those puppy dog eyes. Dean sighed. “I’ll stick around until you leave for college,” he decided. He could wait a couple weeks. Crowley would understand. He’d have to.

The corners of Sam’s lips turned up slightly. “Thanks, Dean.”

“Yeah, yeah.” He rolled his eyes. “You have a dangerous weapon, there, I hope you realize that.”

“I don’t know what you’re talking about,” he denied, but he was smiling. Yeah, bullshit.

Dean’s phone started ringing just a little while later, lighting up with a number he didn’t recognize. He frowned as he answered. “Hello?” he said cautiously. If Crowley was calling him when he _knew_ that he was with his brother, he was going to kill him.

“Hey, brother,” Benny’s voice greeted him.

“Benny!” A smile spread across his face. “Hey. How’s freedom treating you?”

“It’s goin’ to take some getting used to, but anything beats Purgatory, am I right?”

“Definitely,” Dean agreed fervently. And he was pretty sure he understood what Benny was getting at. The excuse he had given Sam as to why he didn’t want to move in with Bobby wasn’t a complete lie, after all – he didn’t feel like the same person he had been before all this crap had started happening. Except, the way he had described it wasn’t quite accurate. It wasn’t that he felt like prison had _changed_ him, rather he felt that it had shown him the kind of person he truly was. “We should get together sometime – grab a drink.”

“Tell me a time and place, and I’ll be there.”

“Will do. Hey, I’m hanging with my brother right now. Talk to you later?”

“Sure. You behave yourself, chief.”

“Yeah,” Dean snorted. “You too,” he said as he hung up the phone, slipping it back into his pocket.

A glance to Sam showed that he was regarding him with a frown. “Who was that?” he asked, his voice more concerned than curious.

“Benny – he was my cellmate. He’s out on parole.”

“And you’re still talking to him?” Sam asked in disbelief.

Dean’s eyebrows furrowed in confusion. “Yeah. He’s my friend.”

“From prison,” he said as though that completely disqualified Dean’s statement.

“Yeah. From prison. Which was where I was, in case you didn’t remember,” he said pointedly, unable to believe what Sam was getting at.

“But you’re different,” Sam disagreed.

“How do you know that?” he demanded indignantly. “You don’t know anything about Benny.”

“Okay, fine. Why was he in prison, then?” he asked reasonably.

“Because he was a pirate. I mean, how cool is that?”

“That’s… not cool at all, Dean.” Sam shook his head. “That’s really disturbing, actually.”

“Oh, come on. He’s reformed,” Dean added.

“So he says.”

“So…” He shook his head in disbelief, realizing that Sam wasn’t going to relent on this. He’d just have to get him to meet Benny one of these days, and then he’d be able to see the kind of person he really was.  “Look,” he sighed. “Arguing with you really isn’t how I want to spend my first day out of prison.”

Sam nodded, his expression softening. “Yeah, me neither.”

“So, onto a subject that matters, then,” Dean forced his voice to be more upbeat. “How much alcohol does Bobby have in the house?”

He chuckled. “He stocked up yesterday – plenty of beer and whiskey.”

“Awesome.”

Just as Sam said, Dean found an ample supply awaiting them when they arrived at the house. Bobby pulled him into a tight hug the moment he walked into the kitchen, only pulling away to pretend to be disapproving when Sam reached for a beer from the fridge.

“Just what do you think you’re doing, boy?” he demanded, rounding on him.

Dean chuckled, not paying much attention to the snarky remark Sam was making as he retreated a few steps to check his phone. He wasn’t at all surprised to see the new message from an unknown number.

‘Enjoying the fresh air? – C’

With a quick glance up to ensure that Sam and Bobby weren’t paying attention, he typed out a quick reply. ‘Hell yeah. Sam wants me to stick around until he leaves for Stanford. Hope that’s ok.’ If it wasn’t, he could deal with it.

He slipped his phone back into his pocket, looking up as Sam took a drink of his beer, then walked over to claim a seat at the table.

“You gonna have a beer, or should I get down a second glass?” Bobby asked him as he started pouring himself a glass a whiskey.

“Get a glass,” he said decidedly. He could use something a little stronger than beer right about now.

He got down a second glass and poured it for him, then they both joined Sam at the table. They drank and joked around for a good couple of hours, and Dean reveled in the feeling of being back with his family.

He managed to find a spare minute while Sam and Bobby were engaged in conversation to check his phone again and read Crowley’s reply. ‘I’ll make due. Just let me know when you’re planning on moving in.’ He barely stopped himself from shaking his head as he finished reading. Moving in with Crowley. He must be insane. But really, it made the most sense. He would be able to stay there rent free, he was already working closely with the guy, and there were… other benefits. He just hoped that they wouldn’t end up killing each other in the first week.

“I gotta admit,” Dean started a little while later, after Bobby had excused himself to go to the bathroom (to which Dean had given him a hard time about not being able to hold his liquor in his old age). “I’m a little sad Alastair’s not at the prison anymore. I would’ve loved to see the look on his face when I got released.”

Sam grinned. “Well, you still got that satisfaction from Crowley, though, right?”

“Uh… not exactly.” He bought himself time by taking another drink – he had moved onto beer after his first glass. “He was pretty cool about it.”

“Really?” he asked skeptically.

“Yeah. The thing about Crowley – all he cares about is the value people bring him.” And Dean needed to remember that. He had told Castiel that he wasn’t in any danger of forgetting, but every once in a while, during a particularly intimate moment, he would find himself thinking that _maybe_ that wasn’t the case with him. But it was. The only reason Crowley cared about him so much was because he thought he’d be useful. “I shoved that journal entry in his face, and he couldn’t do anything with me. So, I wasn’t exactly bringing him any value, was I?”

“Guess not.” Sam shrugged. “What did he want with you, anyway?”

“Dunno,” he lied. “He never got around to making his demands.”

“Aren’t you curious?”

“’Course, but…” He shrugged. “Nothing I can do about it. Not like I can just call him up and ask.”

“True,” Sam sighed. “So… he never hurt you or anything?”

“No.” Dean shook his head. “He was actually pretty good to me, all things considered. Guess he figured I got beat enough by all the other guards.”

“Yeah, Sam told me you had a hell of a time in that prison,” Bobby commented as he reentered the room.

“Yeah, that’s putting it lightly,” he chuckled.

He nodded as he sat down, picking up his glass. “Well, you boys have sure been through a lot of crap this past year. Hopefully this is the start of things improving for you two.”

“I’ll drink to that,” Dean said raising his bottle.

“Me too,” Sam agreed, doing the same.

And maybe Bobby was right. Sam was going off to college. Dean had a well-paying job that wasn’t exactly legal, but he already knew he was damn good at it. There was definitely potential for some form of happiness for the both of them. Maybe things would turn out for the best.

**Notes for the Chapter:**

> Thanks for reading! I hope you enjoyed! I'll start working on the sequel shortly - the working title is 'Just Business'. Or I might end up making that the series title, I haven't decided yet.
> 
> EDIT: The sequel, 'Deal With the Devil' is up.
> 
> Comments and Kudos bring me life and are much appreciated.


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